JPS62114938A - 1-bromo-2-chloro-4-fluoro-5-nitrobenzene and production thereof - Google Patents
1-bromo-2-chloro-4-fluoro-5-nitrobenzene and production thereofInfo
- Publication number
- JPS62114938A JPS62114938A JP25547385A JP25547385A JPS62114938A JP S62114938 A JPS62114938 A JP S62114938A JP 25547385 A JP25547385 A JP 25547385A JP 25547385 A JP25547385 A JP 25547385A JP S62114938 A JPS62114938 A JP S62114938A
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- bromo
- nitrobenzene
- fluoro
- present
- 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.)
- Granted
Links
Landscapes
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、１−ブロモ−２−クロロ−４−フルオロ−５
−ニトロベンゼン（以下本発明化合物と称する。）およ
びその製造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention provides 1-bromo-2-chloro-4-fluoro-5
-Nitrobenzene (hereinafter referred to as the compound of the present invention) and its production method.
本発明化合物は、除草効力を有する一般式〔Ｉ〕Ｃ＝Ｃ
−Ｒ
〔式中、Ｒは水素原子、アｌレギ／ｌ／基または）工二
ル基を表わすっ 〕
で示されるテトラヒドロフタルイミド誘導体の製造中間
体として有用な化合物である。The compound of the present invention has the general formula [I]C═C having herbicidal activity.
-R [wherein R represents a hydrogen atom, an aryl/l/ group, or a hydroxyl group] This is a compound useful as an intermediate for producing a tetrahydrophthalimide derivative.
本発明者らは、除草活性を有する一般式〔Ｉ〕で示され
る化合物の製造法について検討した拮果、本発明化合物
である１−ブロモ−２−クロロ−４−フルオロ−５−ニ
トロベンゼンが上記一般式〔■〕で示される化合物の中
間体として重要であることおよび本発明化合物が１−ブ
ロモ−２−クロロ−４−フルオロベンゼンをニトロ化さ
せることによって有利に製造できることを見い出し本発
明に坐った。The present inventors investigated the method for producing a compound represented by general formula [I] having herbicidal activity, and found that 1-bromo-2-chloro-4-fluoro-5-nitrobenzene, which is a compound of the present invention, was as described above. The inventors of the present invention have discovered that the compound of the present invention is important as an intermediate for the compound represented by the general formula [■] and that the compound of the present invention can be advantageously produced by nitrating 1-bromo-2-chloro-4-fluorobenzene. Ta.
以下に本発明化合物の製造法につき説明する。The method for producing the compound of the present invention will be explained below.
本発明の製造法において、本ニトロ化反応に供される試
剤の量は、１−ブロモ−２− りａ ａ−４−フルオロ
ベンゼン１当量に対して、硫酸は、１当量以上、硝酸は
１．０〜１．２当量である。In the production method of the present invention, the amount of reagents used in the nitration reaction is 1 equivalent or more of sulfuric acid and 1 equivalent of nitric acid per 1 equivalent of 1-bromo-2-a-4-fluorobenzene. .0 to 1.2 equivalents.
ま、ｔ、反応に供される硫酸としては、濃硫酸が好まし
く、硝酸としては発煙硝酸が好ましい。Well, the sulfuric acid used in the reaction is preferably concentrated sulfuric acid, and the nitric acid is preferably fuming nitric acid.
本発明において反応温度および反応時間は、通常夫々−
１０〜２０℃の範囲、１〜１０時間°の範囲で充分目的
を達することができる。反応終了後、反応液を氷水に注
いだ後、水に難溶な有機溶媒による抽出、水洗、濃縮等
の通常の後処理操作を行なうか、さらに必要ならば、再
結晶、クロマトグツフィー等の通常の精製操作によって
目的の１−ブロモ−２−クロロ−４−一フルオロー５−
ニトロベンゼンを得ることができる。In the present invention, the reaction temperature and reaction time are usually -
The purpose can be sufficiently achieved within the range of 10 to 20°C and for 1 to 10 hours. After the reaction is completed, the reaction solution is poured into ice water and then subjected to normal post-treatment operations such as extraction with an organic solvent that is sparingly soluble in water, washing with water, and concentration, or, if necessary, recrystallization, chromatography, etc. The desired 1-bromo-2-chloro-4-1fluoro-5-
Nitrobenzene can be obtained.
なお、本発明の製造法によって得られる本発明化合物か
ら例えば、下記ルー）Ｋよって一般式（１１で示される
除草効力を有する化合物が得られる。Note that from the compound of the present invention obtained by the production method of the present invention, for example, a compound having a herbicidal activity represented by the general formula (11) can be obtained by the following R)K.
Ｂｒ Ｂｒ〔■〕（本発明
化合物） 〔■〕
（ｒｖ’）
Ｃ：、Ｃ−Ｒ
〔Ｉ〕
尚、１−ブロモ−２−クロロ−４−フルオロ−５−ニト
ロベンゼンの原料である１−ブロモ−２−クロロ−４−
フルオロアニリンｄ以下（０製造法によって得ることが
できる。Br Br [■] (Compound of the present invention) [■] (rv') C:, C-R [I] In addition, 1-bromo, which is a raw material for 1-bromo-2-chloro-4-fluoro-5-nitrobenzene -2-chloro-4-
Fluoroaniline d or less (can be obtained by the 0 production method.
用させて臭素化させることによって１−ブロモ−２−ク
ロロ−４−フルオロベンゼンが得られる。上記反応にお
いて反応温度および反応時間は、ジアゾ化は通常夫々−
５〜５Ｃの範囲、０．５〜８時間の範囲、又臭素化は、
通常夫々、２０〜７０℃の範囲、１〜５時間の範囲で充
分目的を達することができる。1-bromo-2-chloro-4-fluorobenzene is obtained by bromination using In the above reaction, the reaction temperature and reaction time are usually -
5-5C range, 0.5-8 hours, and bromination:
Usually, the objective can be sufficiently achieved within the range of 20 to 70°C and for 1 to 5 hours.
上記２−クロロ−４−フルオロアニリンは、Ｆｉｎｇｅ
ｒ ｅｔ ａｌ、 、 Ｊ、 Ａｍ、Ｃｈｅｍ、 Ｓｏ
ｃ、、 ８１ 。The above 2-chloro-4-fluoroaniline is
r et al., , J., Am., Chem., So.
c., 81.
９４（１９５９）に記載の製造法によって製造すること
ができる＠
以下に実施例および参考例をあげて本発明をさらに詳し
く説明する。94 (1959). The present invention will be described in more detail below with reference to Examples and Reference Examples.
実施例
■−プロモー２−クロロー４−フＭオロベンゼン２１ｆ
Ｉ７ｋｉＩｉｌＩ硫酸４０−に溶解させた。Example ■ - Promo 2-chloro-4-F M olobenzene 21f
It was dissolved in I7kiIilI sulfate 40-.
これを０℃〜１０℃に冷却し、発煙硝酸（ｄ＝１．５２
）８．２ｊＦと濃硫酸５−との混合物を０℃〜５℃で徐
々て滴下し、８０分間同温度で攪拌した。この反応混合
物を氷水に注ぎ、エーテルで抽出した。抽出液を水洗、
乾燥、濃縮１．．１−ブロモ−２−クロロ−４−フルオ
ロ−５−ニトロベンゼン１４．８ｇを得り。This was cooled to 0°C to 10°C, and fuming nitric acid (d=1.52
) A mixture of 8.2jF and concentrated sulfuric acid 5- was gradually added dropwise at 0°C to 5°C, and stirred at the same temperature for 80 minutes. The reaction mixture was poured into ice water and extracted with ether. Wash the extract with water,
Drying, concentration 1. ．． 14.8 g of 1-bromo-2-chloro-4-fluoro-5-nitrobenzene was obtained.
６５．０−６５．５℃
参考例
２−クロロ−４−フルオロアニリン５８ｆをａ硫酸１２
０ｇおよび水１６０−の混合物に溶かし、−５℃〜Ｏ℃
で亜硝酸ナトリウム２８ｆを水ＩＱＱｍｊに溶かした溶
液を加え、２０分間同じ温度で攪拌した。反応液中の過
剰の亜硝酸と、ヨウ化カリ澱粉紙の呈色がなくなるまで
、反応液にスルファミン酸を加えることによって除いた
後、この得られたジアゾニウム溶液を臭化第一銅６８ｇ
を４８％臭化水素酸水溶液５００−に溶かした溶液に室
温で加え、８０〜４０℃で８０分間攪拌した。65.0-65.5℃ Reference Example 2-Chloro-4-fluoroaniline 58f was mixed with a sulfuric acid 12
Dissolved in a mixture of 0 g and 160 g of water and heated to -5°C to 0°C.
A solution of sodium nitrite 28f dissolved in water IQQmj was added thereto, and the mixture was stirred at the same temperature for 20 minutes. Excess nitrous acid in the reaction solution was removed by adding sulfamic acid to the reaction solution until the color of the potassium iodide starch paper disappeared, and the resulting diazonium solution was mixed with 68 g of cuprous bromide.
was added to a solution prepared by dissolving 500% of a 48% aqueous hydrobromic acid solution at room temperature, and the mixture was stirred at 80 to 40°C for 80 minutes.
Claims (2)
トロベンゼン(1) 1-bromo-2-chloro-4-fluoro-5-nitrobenzene
をニトロ化させることを特徴とする１−ブロモ−２−ク
ロロ−４−フルオロ−５−ニトロベンゼンの製造法(2) A method for producing 1-bromo-2-chloro-4-fluoro-5-nitrobenzene, which comprises nitrating 1-bromo-2-chloro-4-fluorobenzene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25547385A JPH0653709B2 (en) | 1985-11-14 | 1985-11-14 | 1-Bromo-2-chloro-4-fluoro-5-nitrobenzene and process for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25547385A JPH0653709B2 (en) | 1985-11-14 | 1985-11-14 | 1-Bromo-2-chloro-4-fluoro-5-nitrobenzene and process for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62114938A true JPS62114938A (en) | 1987-05-26 |
| JPH0653709B2 JPH0653709B2 (en) | 1994-07-20 |
Family
ID=17279253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25547385A Expired - Lifetime JPH0653709B2 (en) | 1985-11-14 | 1985-11-14 | 1-Bromo-2-chloro-4-fluoro-5-nitrobenzene and process for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0653709B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1298697C (en) * | 2003-12-03 | 2007-02-07 | 上海化学试剂研究所 | Method for preparing 4-bromine-5-fluorine-2-nitro methylbenzene |
-
1985
- 1985-11-14 JP JP25547385A patent/JPH0653709B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1298697C (en) * | 2003-12-03 | 2007-02-07 | 上海化学试剂研究所 | Method for preparing 4-bromine-5-fluorine-2-nitro methylbenzene |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0653709B2 (en) | 1994-07-20 |
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