JP3102151B2 - Iodinated benzyldiphenyl and its preparation - Google Patents
Iodinated benzyldiphenyl and its preparationInfo
- Publication number
- JP3102151B2 JP3102151B2 JP04228414A JP22841492A JP3102151B2 JP 3102151 B2 JP3102151 B2 JP 3102151B2 JP 04228414 A JP04228414 A JP 04228414A JP 22841492 A JP22841492 A JP 22841492A JP 3102151 B2 JP3102151 B2 JP 3102151B2
- Authority
- JP
- Japan
- Prior art keywords
- benzyldiphenyl
- acid
- compound
- benzyl
- mol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Photoreceptors In Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、新規なヨウ素化ベンジ
ルジフェニルおよびその製法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel iodinated benzyldiphenyl and a method for producing the same.
【０００２】[0002]
【従来の技術】ベンジルジフェニルのモノヨウ素化物で
ある４−ベンジル−４’−ヨードジフェニル化合物また
はジヨウ素化物である４−ｐ−ヨードベンジル−４’−
ヨードジフェニル化合物は知られていない。2. Description of the Related Art 4-benzyl-4'-iododiphenyl compound which is a monoiodide of benzyldiphenyl or 4-p-iodobenzyl-4'- which is a diiodide
No iododiphenyl compounds are known.
【０００３】[0003]
【発明が解決しようとする課題】本発明はベンジルジフ
ェニルのモノヨウ素化物である４−ベンジル−４’−ヨ
ードジフェニル化合物またはジヨウ素化物である４−ｐ
−ヨードベンジル−４’−ヨードジフェニル化合物およ
びその製造方法を提供すること目的とする。SUMMARY OF THE INVENTION The present invention relates to a 4-benzyl-4'-iododiphenyl compound which is a monoiodide of benzyldiphenyl or 4-p which is a diiodide of 4-benzyl-4'-iododiphenyl.
An object is to provide a -iodobenzyl-4'-iododiphenyl compound and a method for producing the same.
【０００４】[0004]
【課題を解決するための手段】本発明は下記構造式
［Ｉ］で示される４−ベンジル−４’−ヨードジフェニ
ル化合物；The present invention provides a 4-benzyl-4'-iododiphenyl compound represented by the following structural formula [I]:
【化５】 下記構造式［ＩＩ］で示される４−ｐ−ヨードベンジル
−４’−ヨードジフェニル化合物Embedded image 4-p-iodobenzyl-4′-iododiphenyl compound represented by the following structural formula [II]
【化６】 およびそれらの製造方法に関する。Embedded image And their manufacturing methods.
【０００５】上記式中、Ｒ1〜Ｒ3はそれぞれ独立して、
水素原子、アルキル基またはアルコキシ基を示す。In the above formula, R 1 to R 3 are each independently
It represents a hydrogen atom, an alkyl group or an alkoxy group.
【０００６】本発明のヨウ素化ベンジルジフェニル化合
物は、例えばアルキル化アミン等と反応させて、アミノ
化し、電子写真感光体等の電荷輸送物質として使用する
ことができる。また、その他に有機精密化学品、例えば
ヒドロキシベンジルジフェニル化合物の合成原料として
使用可能である。The iodinated benzyldiphenyl compound of the present invention can be aminated by reacting it with, for example, an alkylated amine or the like, and used as a charge transport material for an electrophotographic photoreceptor or the like. In addition, it can be used as a raw material for synthesizing organic fine chemicals such as hydroxybenzyldiphenyl compounds.
【０００７】本発明のヨウ素化ベンジルジフェニル化合
物は、主に上記したような用途物への中間体として有用
な化合物であり、最終目的物への変換のためには、ヨウ
素化物が最も適している。The iodinated benzyldiphenyl compound of the present invention is a compound useful mainly as an intermediate for the above-mentioned applications, and the iodide is most suitable for conversion to the final product. .
【０００８】構造式［Ｉ］および［ＩＩ］に示すヨウ素
化ベンジルジフェニル化合物は、以下に示すように、ベ
ンジルジフェニル化合物を直接ヨウ素化することによっ
て製造することができる；The iodinated benzyl diphenyl compounds represented by the structural formulas [I] and [II] can be produced by directly iodinating a benzyl diphenyl compound as shown below:
【０００９】[0009]
【化７】 上記式中、Ｒ1〜Ｒ3はそれぞれ独立して、水素原子、ア
ルキル基またはアルコキシ基を示す。Embedded image In the above formula, R 1 to R 3 each independently represent a hydrogen atom, an alkyl group or an alkoxy group.
【００１０】上記反応におけるヨウ素化反応は逐次反応
であり、４−ベンジル−４’−ヨードビフェニル（構造
式［Ｉ］）の化合物ができ、その後に４−ｐ−ヨードベ
ンジル−４’−ヨードビフェニル（構造式［ＩＩ］）の
化合物ができる。化合物［Ｉ］と化合物［ＩＩ］の割合
はヨウ素化剤の量と反応時間で調整することができる。[0010] The iodination reaction in the above reaction is a sequential reaction, and a compound of 4-benzyl-4'-iodobiphenyl (structural formula [I]) is formed, followed by 4-p-iodobenzyl-4'-iodobiphenyl. A compound of (Structural Formula [II]) is obtained. The ratio of compound [I] to compound [II] can be adjusted by the amount of the iodinating agent and the reaction time.
【００１１】ヨウ素化剤としては、ヨウ素、ヨウ化カ
リ、ヨウ素酸カリ、過ヨウ素酸等が用いられる。この中
でも特にヨウ素と過ヨウ素酸を併用することが好まし
い。As the iodinating agent, iodine, potassium iodide, potassium iodate, periodic acid and the like are used. Among them, it is particularly preferable to use iodine and periodic acid in combination.
【００１２】ヨウ素化剤の使用量は、広い範囲から適宜
選択されるが、収率よく本発明のヨウ素化ベンジルジフ
ェニル化合物を得るには、ベンジルジフェニルに対して
ヨウ素化剤の割合を１／２モル量ないし過剰モル量用い
るのがよい。特に、モノヨウ素化合物［Ｉ］を優先的に
合成したい場合は、ヨウ素化剤の使用量はベンジルジフ
ェニル１モルに対して１／２モル以下の割合で使用し、
ヨウ素化合物［ＩＩ］を優先的に合成したい場合は、ヨ
ウ素化剤の使用量はベンジルジフェニル１モルに対して
１／２モル以上の割合で使用することが好ましい。ヨウ
素化剤は、反応初期から全量反応系に加えてもよいし、
反応の進行とともに逐次添加してもよい。The amount of the iodinating agent used is appropriately selected from a wide range, but in order to obtain the iodinated benzyldiphenyl compound of the present invention in good yield, the ratio of the iodinating agent to benzyldiphenyl should be 1/2. It is preferable to use a molar amount or an excess molar amount. In particular, when preferentially synthesizing the monoiodine compound [I], the amount of the iodinating agent used is 1/2 mol or less per 1 mol of benzyldiphenyl,
When it is desired to synthesize the iodine compound [II] preferentially, the amount of the iodination agent used is preferably at least 1/2 mol per 1 mol of benzyldiphenyl. The iodination agent may be added to the reaction system in its entirety from the beginning of the reaction,
You may add sequentially as reaction progresses.
【００１３】本発明の化合物合成においては、反応触媒
として酸化剤、例えば過酸化水素、過硫酸塩類を添加し
てもよい。添加量はベンジルジフェニル１モルに対して
１／２０モル〜２０モル、好ましくは１／１０〜１０モ
ルである。２０モルより多いと副反応が起こりやすく収
率が悪くなり、１／２０モルより少ないと触媒としての
効果が少ない。In the compound synthesis of the present invention, an oxidizing agent such as hydrogen peroxide or persulfate may be added as a reaction catalyst. The addition amount is 1/20 mol to 20 mol, preferably 1/10 to 10 mol, per 1 mol of benzyldiphenyl. If it is more than 20 moles, side reactions are likely to occur, and the yield will be poor. If it is less than 1/20 moles, the effect as a catalyst will be small.
【００１４】上記反応は、酸性下で行うことが望ましく
プロトン酸を所定量用いる。プロトン酸としては、酢
酸、硫酸、硝酸、クロル酢酸、トリフルオロ酢酸および
それらの混合物等が用いられる。これらの中でも、特に
酢酸、硝酸、トリフルオロ酢酸が好ましい。プロトン酸
は酸化剤としても作用し触媒の働きをする。プロトン酸
の使用量は、用いるプロトン酸の種類により異なるが、
前記プロトン酸の働きよりして、例えば反応溶液のｐＨ
で表して、４以下となるように使用量を調整すればよ
い。The above reaction is desirably carried out under acidic conditions, and a predetermined amount of a protonic acid is used. As the protic acid, acetic acid, sulfuric acid, nitric acid, chloroacetic acid, trifluoroacetic acid and a mixture thereof are used. Of these, acetic acid, nitric acid, and trifluoroacetic acid are particularly preferred. Protonic acids also act as oxidants and act as catalysts. The amount of protonic acid used depends on the type of protonic acid used,
Due to the action of the protonic acid, for example, the pH of the reaction solution
And the amount of use may be adjusted so as to be 4 or less.
【００１５】本発明のヨウ素化ベンジルジフェニルの製
法においては、ベンジルジフェニル、ヨウ素化剤および
プロトン酸の所定量を一度に混合処理してもよいし、ベ
ンジルジフェニルとヨウ素化剤を適当な溶媒（例えば
１，２−ジクロルエタン等）の溶媒に溶解した溶液を、
所望により酸化剤を含むプロトン溶媒の溶液に徐々に添
加して反応を行ってもよい。後者の場合、プロトン酸の
使用量が上記範囲となるように注意する必要がある。In the process for producing iodinated benzyldiphenyl of the present invention, a predetermined amount of benzyldiphenyl, an iodinating agent and a protonic acid may be mixed at once, or benzyldiphenyl and an iodinating agent may be mixed with a suitable solvent (for example, 1,2-dichloroethane) in a solvent,
If desired, the reaction may be carried out by gradually adding to a solution of a proton solvent containing an oxidizing agent. In the latter case, care must be taken so that the amount of protonic acid used is within the above range.
【００１６】反応は、５０〜１００℃の温度で１〜５０
時間行えば十分であるが、反応終了は、ＴＬＣ、液体ク
ロマトグラフィー等の方法により確認することができ
る。そして、ジフェニルおよびベンジルのいずれもｐ位
が酸化にたいして活性であるため、上記した製法におい
ては、その部位がヨウ素化される。The reaction is carried out at a temperature of 50-100 ° C. for 1-50.
Time is sufficient, but the completion of the reaction can be confirmed by a method such as TLC or liquid chromatography. Since both diphenyl and benzyl are active at oxidation at the p-position, the site is iodinated in the above-mentioned production method.
【００１７】反応終了後は常法に従い、例えば濾過、濃
縮、結晶化、分別蒸留、再結晶化等の通常の分離手段に
より、反応物から本発明の化合物を得ることができる。After the completion of the reaction, the compound of the present invention can be obtained from the reaction product by a conventional separation method such as filtration, concentration, crystallization, fractional distillation, recrystallization and the like.
【００１８】４−ベンジル−４’−ヨードビフェニル
（構造式［Ｉ］）の化合物と４−ｐ−ヨードベンジル−
４’−ヨードビフェニル（構造式［ＩＩ］）とが混合物
で得られる場合は、ガスクロマトグラフィー、液体クロ
マトグラフィー、カラムクロマトグラフィー等の手段
で、両者を分離することができる。A compound of 4-benzyl-4'-iodobiphenyl (structural formula [I]) and 4-p-iodobenzyl-
When 4'-iodobiphenyl (structural formula [II]) is obtained as a mixture, both can be separated by means such as gas chromatography, liquid chromatography, column chromatography and the like.
【００１９】[0019]
【実施例】以下、実施例により本発明をさらに具体的に
説明する。The present invention will be described more specifically with reference to the following examples.
【００２０】実施例１ 水冷冷却管を設けた３００ｍｌの容器に、ベンジルジフ
ェニル２４．４ｇ（０．１モル）、メタ過ヨウ素酸・二
水和物５ｇ（０．０２２モル）、ヨウ素１３ｇ（０．０
５１モル）、酢酸４９ｍｌ、水１０ｍｌおよび濃硫酸
１．５ｍｌを入れて混合した。該混合物を７０℃で３時
間撹拌し反応を終了した。Example 1 In a 300 ml container equipped with a water-cooled cooling tube, 24.4 g (0.1 mol) of benzyldiphenyl, 5 g (0.022 mol) of metaperiodic acid dihydrate, and 13 g of iodine (0 mol) .0
51 mol), 49 ml of acetic acid, 10 ml of water and 1.5 ml of concentrated sulfuric acid. The mixture was stirred at 70 ° C. for 3 hours to complete the reaction.
【００２１】得られた反応混合物を亜硫酸ソーダ水で洗
浄し、３００ｍｌのトルエンで２回抽出した。得られた
トルエン層を飽和食塩水で洗浄後、硫酸マグネシウムで
乾燥した。その後、トルエン層を濃縮し、４−ベンジル
−４’−ヨードビフェニルとベンジルジフェニルとの混
合物からなる結晶を２８．５ｇ得た。減圧蒸留によりベ
ンジルジフェニルを取り除き、４−ベンジル−４’−ヨ
ードビフェニルからなる白色針状２５．３ｇを得た。融
点は１１４〜１１６℃であった。The resulting reaction mixture was washed with aqueous sodium sulfite and extracted twice with 300 ml of toluene. The obtained toluene layer was washed with saturated saline and dried over magnesium sulfate. Thereafter, the toluene layer was concentrated to obtain 28.5 g of a crystal composed of a mixture of 4-benzyl-4′-iodobiphenyl and benzyldiphenyl. Benzyldiphenyl was removed by distillation under reduced pressure to obtain 25.3 g of white needles composed of 4-benzyl-4′-iodobiphenyl. The melting point was 114-116 ° C.
【００２２】得られた化合物の赤外吸収スペクトルを図
１に示す。測定は、モデル１７１０ＦＴＩＲ（パーキン
エルマー社製）を用い、解像度４ｃｍ-1で５回スキャン
することにより行った。FIG. 1 shows the infrared absorption spectrum of the compound obtained. The measurement was performed using a model 1710FTIR (manufactured by PerkinElmer) by scanning 5 times at a resolution of 4 cm -1 .
【００２３】実施例２ ベンジルジフェニル２４．４ｇ（０．１モル）、ヨウ素
２５．４ｇ（０．１モル）、１、２−ジクロルエタン５
００ｇを、容量１リットルのガラス製４つ口フラスコに
入れた。混合物を８０℃の温度まで加熱し溶解させた。Example 2 24.4 g (0.1 mol) of benzyldiphenyl, 25.4 g (0.1 mol) of iodine, 1,2-dichloroethane 5
00 g was placed in a 1 liter glass four-necked flask. The mixture was heated to a temperature of 80 ° C. to dissolve.
【００２４】次に、３５重量％の過酸化水素４８．５ｇ
と９７重量％硫酸１０１ｇを室温下で混合して混合液を
調製した。Next, 48.5 g of 35% by weight of hydrogen peroxide.
And 97 g of 97% by weight sulfuric acid were mixed at room temperature to prepare a mixed solution.
【００２５】得られた混合液を、４つ口フラスコに撹拌
下３０分で滴下し、さらに４時間撹拌した。The obtained mixture was dropped into a four-necked flask over 30 minutes with stirring, and further stirred for 4 hours.
【００２６】反応終了後、２層分離し、油層を飽和食塩
水で洗浄後、硫酸マグネシウムで乾燥した。その後、
１、２−ジクロルエタンを除去することにより、ベンジ
ルジフェニルと４−ベンジル−４’−ヨードビフェニル
とからなる混合物を得た。減圧蒸留によりベンジルジフ
ェニルを取り除き、４−ベンジル−４’−ヨードビフェ
ニル２０．７ｇを得た。After completion of the reaction, two layers were separated, and the oil layer was washed with saturated saline and dried over magnesium sulfate. afterwards,
By removing 1,2-dichloroethane, a mixture consisting of benzyldiphenyl and 4-benzyl-4′-iodobiphenyl was obtained. Benzyldiphenyl was removed by distillation under reduced pressure to obtain 20.7 g of 4-benzyl-4′-iodobiphenyl.
【００２７】実施例３ ベンジルジフェニル２４．４ｇ（０．１モル）、ヨウ素
酸カリ４．７ｇ（０．０２２モル）、ヨウ化カリウム１
６．６ｇ（０．１モル）、酢酸８０ｍｌ、水１０ｍｌお
よび濃硫酸１．５ｍｌを混合し、８０℃で４時間撹拌し
た。Example 3 24.4 g (0.1 mol) of benzyldiphenyl, 4.7 g (0.022 mol) of potassium iodate, potassium iodide 1
6.6 g (0.1 mol), 80 ml of acetic acid, 10 ml of water and 1.5 ml of concentrated sulfuric acid were mixed and stirred at 80 ° C. for 4 hours.
【００２８】得られた反応混合物を亜硫酸ソーダ水で洗
浄し、３００ｍｌのトルエンで２回抽出した。得られた
トルエン層を飽和食塩水で洗浄後、硫酸マグネシウムで
乾燥した。乾燥したトルエン層を濃縮することにより、
ベンジルジフェニルと４−ベンジル−４’−ヨードビフ
ェニルとからなる混合物を得た。減圧蒸留によりベンジ
ルジフェニルを取り除き、４−ベンジル−４’−ヨード
ビフェニル２４．６ｇを得た。The obtained reaction mixture was washed with aqueous sodium sulfite and extracted twice with 300 ml of toluene. The obtained toluene layer was washed with saturated saline and dried over magnesium sulfate. By concentrating the dried toluene layer,
A mixture consisting of benzyldiphenyl and 4-benzyl-4'-iodobiphenyl was obtained. Benzyldiphenyl was removed by distillation under reduced pressure to obtain 24.6 g of 4-benzyl-4′-iodobiphenyl.
【００２９】実施例４ 水冷冷却管を設けた３００ｍｌの容器に、ベンジルジフ
ェニル２４．４ｇ（０．１モル）、メタ過ヨウ素酸・二
水和物１０ｇ（０．０４４モル）、ヨウ素２５ｇ（０．
１モル）、トリフルオロ酢酸５０ｍｌ、水１０ｍｌおよ
び濃硫酸１．５ｍｌを入れて混合した。該混合物を８０
℃で１日撹拌し反応を終了した。Example 4 In a 300 ml vessel equipped with a water-cooled cooling tube, 24.4 g (0.1 mol) of benzyldiphenyl, 10 g (0.044 mol) of metaperiodic acid dihydrate, 25 g of iodine (0 mol) .
1 mol), 50 ml of trifluoroacetic acid, 10 ml of water and 1.5 ml of concentrated sulfuric acid. 80 of this mixture
The reaction was completed by stirring at ° C for 1 day.
【００３０】得られた反応混合物を亜硫酸ソーダ水で洗
浄し、３００ｍｌのジクロルメタンで２回抽出した。得
られたジクロルメタン層を飽和食塩水で洗浄後、硫酸マ
グネシウムで乾燥した。その後、ジクロルメタンを留去
し、４−ベンジル−４’−ヨードビフェニルと４−ｐ−
ヨードベンジル−４’−ヨードビフェニルとの混合物を
得た。The obtained reaction mixture was washed with aqueous sodium sulfite and extracted twice with 300 ml of dichloromethane. The obtained dichloromethane layer was washed with saturated saline and dried over magnesium sulfate. Thereafter, dichloromethane was distilled off, and 4-benzyl-4′-iodobiphenyl and 4-p-
A mixture with iodobenzyl-4'-iodobiphenyl was obtained.
【００３１】液体クロマトグラフィーにより、上記混合
物を分析した結果、ベンジルジフェニルの転化率は、１
００％であり、４−ｐ−ヨードベンジル−４’−ヨード
ビフェニルは８３％、４−ベンジル−４’−ヨードビフ
ェニルは１６％であった。As a result of analyzing the above mixture by liquid chromatography, the conversion of benzyldiphenyl was found to be 1
00%, 83% for 4-p-iodobenzyl-4'-iodobiphenyl and 16% for 4-benzyl-4'-iodobiphenyl.
【００３２】上記混合物をシリカゲルクロマトグラフィ
ー（溶媒：トルエン／ヘキサン）に付し両者を分離し、
エタノールより再結し、４−ｐ−ヨードベンジル−４’
−ヨードビフェニルの白色針状結晶１５ｇを得た。融点
は１５５〜１５８℃であった。 得られた化合物の赤外
吸収スペクトルを図２に示す。測定は実施例１における
のと同様に行った。The mixture was subjected to silica gel chromatography (solvent: toluene / hexane) to separate the two,
Reconstituted with ethanol, 4-p-iodobenzyl-4 ′
15 g of white needle crystals of iodobiphenyl were obtained. Melting point was 155-158 ° C. FIG. 2 shows the infrared absorption spectrum of the obtained compound. The measurement was performed in the same manner as in Example 1.
【００３３】[0033]
【発明の効果】本発明は新規なベンジルジフェニルのヨ
ウ化物およびその製造方法を提供した。本発明のベンジ
ルジフェニルのヨウ化物は、機能性材料、特に電荷輸送
材料の中間体として有用である。The present invention provides a novel iodide of benzyldiphenyl and a method for producing the same. The benzyldiphenyl iodide of the present invention is useful as an intermediate of a functional material, particularly a charge transport material.
【図１】 ４−ベンジル−４’−ヨードビフェニルの赤
外吸収スペクトルを表す図である。FIG. 1 is a diagram showing an infrared absorption spectrum of 4-benzyl-4′-iodobiphenyl.
【図２】 ４−ｐ−ヨードベンジル−４’−ヨードビフ
ェニルの赤外吸収スペクトルを表す図である。FIG. 2 is a diagram showing an infrared absorption spectrum of 4-p-iodobenzyl-4′-iodobiphenyl.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ // Ｃ０７Ｂ 61/00 ３００ Ｃ０７Ｂ 61/00 ３００ (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 25/18 C07C 17/12 C07C 43/225 C07B 61/00 300 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 7 identification code FI // C07B 61/00 300 C07B 61/00 300 (58) Field surveyed (Int. Cl. 7 , DB name) C07C 25/18 C07C 17/12 C07C 43/225 C07B 61/00 300 CA (STN) REGISTRY (STN)
Claims (5)
ル−４’−ヨードジフェニル； 【化１】 ［式中、Ｒ1〜Ｒ3はそれぞれ独立して、水素原子、アル
キル基またはアルコキシ基を示す］。1. 4-benzyl-4′-iododiphenyl represented by the following structural formula [I]: embedded image [Wherein, R 1 to R 3 each independently represent a hydrogen atom, an alkyl group or an alkoxy group].
ヨードベンジル−４’−ヨードジフェニル； 【化２】 ［式中、Ｒ1〜Ｒ3はそれぞれ独立して、水素原子、アル
キル基またはアルコキシ基を示す］。2. 4-p- represented by the following structural formula [II]
Iodobenzyl-4'-iododiphenyl; [Wherein, R 1 to R 3 each independently represent a hydrogen atom, an alkyl group or an alkoxy group].
触媒としてヨウ素および／またはヨウ素化合物を反応さ
せ下記構造式［Ｉ］または［ＩＩ］で表されるヨウ素化
ベンジルジフェニルを製造する方法； 【化３】 【化４】 ［式中Ｒ1〜Ｒ3はそれぞれ独立して、水素原子、アルキ
ル基またはアルコキシ基を示す］。3. A method for producing iodinated benzyldiphenyl represented by the following structural formula [I] or [II] by reacting iodine and / or an iodine compound with 4-benzyldiphenyl using a protonic acid as a catalyst; ] Embedded image [Wherein R 1 to R 3 each independently represent a hydrogen atom, an alkyl group or an alkoxy group].
酢酸、トリフルオロ酢酸である請求項３記載の方法。4. The method according to claim 3, wherein the protic acid is acetic acid, sulfuric acid, nitric acid, chloroacetic acid, or trifluoroacetic acid.
カリあるいは過ヨウ素酸である請求項３記載の方法。5. The method according to claim 3, wherein the iodine compound is potassium iodide, potassium iodate or periodic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04228414A JP3102151B2 (en) | 1992-08-27 | 1992-08-27 | Iodinated benzyldiphenyl and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04228414A JP3102151B2 (en) | 1992-08-27 | 1992-08-27 | Iodinated benzyldiphenyl and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0672918A JPH0672918A (en) | 1994-03-15 |
| JP3102151B2 true JP3102151B2 (en) | 2000-10-23 |
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ID=16876104
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP04228414A Expired - Fee Related JP3102151B2 (en) | 1992-08-27 | 1992-08-27 | Iodinated benzyldiphenyl and its preparation |
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| JP4174391B2 (en) * | 2002-08-30 | 2008-10-29 | キヤノン株式会社 | Electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
| JP2008247746A (en) * | 2007-03-29 | 2008-10-16 | Mitsubishi Gas Chem Co Inc | Method for producing haloiodoaniline compounds |
| CN105753643B (en) * | 2016-04-29 | 2018-04-20 | 河南省科学院化学研究所有限公司 | A kind of synthetic method of 2,5 2 bromo-iodobenzene |
| JP6861060B2 (en) * | 2017-03-17 | 2021-04-21 | 東レ・ファインケミカル株式会社 | Method for Producing 4,4'-Diiodot-3,3'-Dimethylbiphenyl |
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| Publication number | Publication date |
|---|---|
| JPH0672918A (en) | 1994-03-15 |
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