JP4430943B2 - 2−(クロロメチル)フェニル酢酸誘導体の製造方法 - Google Patents
2−(クロロメチル)フェニル酢酸誘導体の製造方法 Download PDFInfo
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- JP4430943B2 JP4430943B2 JP2003571244A JP2003571244A JP4430943B2 JP 4430943 B2 JP4430943 B2 JP 4430943B2 JP 2003571244 A JP2003571244 A JP 2003571244A JP 2003571244 A JP2003571244 A JP 2003571244A JP 4430943 B2 JP4430943 B2 JP 4430943B2
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- formula
- iron
- indium
- chloride
- alkoxy
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- 0 *C(C(c1c(CN)cccc1)=*O*I)=O Chemical compound *C(C(c1c(CN)cccc1)=*O*I)=O 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
で表される化合物のエーテル開裂によって製造する方法に関する。
実施例1
7.5g(24mmol)のkresoxim-methylを150mlのクロロベンゼンに溶解した。次いで、0.32g(2.4mmol)の塩化鉄(III)を加え、50℃に加熱している段階中、1時間以内に2.6g(72mmol)の塩化水素をガス状で加えた。反応混合物を撹拌しながら50℃にさらに2時間保持し、次いで、HPLCによって転化率を監視した。反応終了後、反応溶液を冷却し、10mlのメタノールと混合した。反応混合物を、まず塩酸で抽出し、次いで水酸化ナトリウムで抽出した。有機相を中性になるまで洗浄し、次いで溶媒を除去した。2-メトキシイミノ-2-[(2-クロロメチル)フェニル]酢酸メチルの収率は75%であった。
7.5g(24mmol)のkresoxim-methylを150 mlのトルエンに溶解した。次いで、0.53g(2.4mmol)の塩化インジウム(III)を加え、40℃に加熱している段階中、1時間以内に2.6g(72mmol)の塩化水素をガス状で加えた。反応混合物を撹拌しながら40℃にさらに4時間保持し、次いで実施例1と同様にして後処理した。2-メトキシイミノ-2-[(2-クロロメチル)フェニル]酢酸メチルの収率は80%であった。
実施例1のエーテル開裂を、150mlの1,2-ジクロロエタン中で繰り返した。100℃に加熱している段階中、1時間以内に4.1g(112mmol)の塩化水素をガス状で加えた。反応混合物を100℃にさらに5時間保持した。生成物の収率は80%であった。
7.5g(24mmol)のkresoxim-methylを、150mlのトルエンに溶解した。次いで、0.32g(2.4mmol)の塩化アルミニウムを加え、100℃に加熱している段階中、1時間以内に2.6g(72mmol)の塩化水素をガス状で加えた。反応混合物を撹拌しながら100℃にさらに2時間保持し、次いで実施例1と同様にして後処理した。生成物の収率は30%であった。
7.5g(24mmol)のkresoxim-methylを150mlの1,2-ジクロロエタンに溶解した。次いで、0.63g(2.4mmol)の四塩化スズを加え、85℃に加熱している段階中、1時間以内に2.6g(72mmol)の塩化水素をガス状で加えた。反応混合物を撹拌しながら85℃にさらに4時間保持し、次いで実施例1と同様にして後処理した。生成物の収率は30%であった。
Claims (5)
- 式I
で表される2-(クロロメチル)フェニル酢酸誘導体を、
式II
で表される化合物のエーテル開裂によって製造する方法であって、
塩化水素および不活性溶媒の存在下で反応を行い、反応混合物に、鉄、鉄ハロゲン化物、鉄酸化物、鉄トリフラート、インジウム、インジウムハロゲン化物、インジウム酸化物、およびインジウムトリフラートからなる群から選択される触媒を添加することを含む、
上記方法。 - 使用される触媒が塩化鉄(III)である、請求項1に記載の方法。
- 1モル当量の式IIで表される化合物に対して、触媒を、0.001〜0.5モル当量の濃度で使用する、請求項1または2に記載の方法。
- 1モル当量の式IIで表される化合物に対して、1〜25モル当量の塩化水素を使用する、請求項1〜3のいずれか1項に記載の方法。
- 使用される不活性溶媒が、ハロゲン化されていてもよい芳香族または脂肪族の炭化水素である、請求項1〜4のいずれか1項に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10208029 | 2002-02-26 | ||
PCT/EP2003/001160 WO2003072538A1 (de) | 2002-02-26 | 2003-02-06 | Verfahren zur herstellung von 2-chlormethylphenylessigsäurederivaten |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009224405A Division JP5308297B2 (ja) | 2002-02-26 | 2009-09-29 | 2−(クロロメチル)フェニル酢酸誘導体の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005518440A JP2005518440A (ja) | 2005-06-23 |
JP4430943B2 true JP4430943B2 (ja) | 2010-03-10 |
Family
ID=27762430
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003571244A Expired - Fee Related JP4430943B2 (ja) | 2002-02-26 | 2003-02-06 | 2−(クロロメチル)フェニル酢酸誘導体の製造方法 |
JP2009224405A Expired - Fee Related JP5308297B2 (ja) | 2002-02-26 | 2009-09-29 | 2−(クロロメチル)フェニル酢酸誘導体の製造方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009224405A Expired - Fee Related JP5308297B2 (ja) | 2002-02-26 | 2009-09-29 | 2−(クロロメチル)フェニル酢酸誘導体の製造方法 |
Country Status (19)
Country | Link |
---|---|
US (1) | US7488840B2 (ja) |
EP (1) | EP1480945B1 (ja) |
JP (2) | JP4430943B2 (ja) |
KR (1) | KR100934521B1 (ja) |
CN (1) | CN1639113B (ja) |
AT (1) | ATE304525T1 (ja) |
AU (1) | AU2003215553B2 (ja) |
BR (1) | BR0307533A (ja) |
CA (1) | CA2476035A1 (ja) |
DE (1) | DE50301191D1 (ja) |
DK (1) | DK1480945T3 (ja) |
EA (1) | EA006653B1 (ja) |
ES (1) | ES2248762T3 (ja) |
IL (1) | IL163111A (ja) |
MX (1) | MXPA04007063A (ja) |
PL (1) | PL205226B1 (ja) |
SI (1) | SI1480945T1 (ja) |
WO (1) | WO2003072538A1 (ja) |
ZA (1) | ZA200407706B (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010031027A (ja) * | 2002-02-26 | 2010-02-12 | Basf Se | 2−(クロロメチル)フェニル酢酸誘導体の製造方法 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090177005A1 (en) * | 2002-02-26 | 2009-07-09 | Basf Aktiengesellschaft | Method For Producing 2-(chloromethyl)penylacetic acid derivatives |
EP2393775B1 (en) | 2009-02-05 | 2014-06-25 | Basf Se | Method for producing 2-halogenomethylphenyl acetic acid derivatives |
CN109748792A (zh) * | 2018-12-24 | 2019-05-14 | 江苏中旗科技股份有限公司 | 啶氧菌酯中间体2-(2-氯甲基苯基)-3-甲氧基丙烯酸甲酯的制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4030038A1 (de) * | 1990-09-22 | 1992-03-26 | Basf Ag | Ortho-substituierte phenylessigsaeureamide |
AU711072B2 (en) * | 1995-12-14 | 1999-10-07 | Basf Aktiengesellschaft | 2-(o-(pyrimidin-4-yl)methylenoxy)phenylacetic acid derivatives and their use for controlling harmful fungi and animal pests |
US6034131A (en) * | 1996-03-08 | 2000-03-07 | Basf Aktiengesellschaft | Diphenylethers, process and intermediate products for their preparation, and their use |
IT1302108B1 (it) | 1997-10-13 | 2000-07-26 | Corob Spa | Gruppo di erogazione per una macchina dispensatrice di prodotti fluidi comprendente una camera pompante a volume variabile, e macchina |
EA006653B1 (ru) * | 2002-02-26 | 2006-02-24 | Басф Акциенгезельшафт | Способ получения производных 2-хлорметилфенилуксусной кислоты |
-
2003
- 2003-02-06 EA EA200401013A patent/EA006653B1/ru not_active IP Right Cessation
- 2003-02-06 PL PL371057A patent/PL205226B1/pl not_active IP Right Cessation
- 2003-02-06 US US10/505,475 patent/US7488840B2/en not_active Expired - Fee Related
- 2003-02-06 AT AT03742928T patent/ATE304525T1/de not_active IP Right Cessation
- 2003-02-06 DE DE50301191T patent/DE50301191D1/de not_active Expired - Lifetime
- 2003-02-06 ES ES03742928T patent/ES2248762T3/es not_active Expired - Lifetime
- 2003-02-06 JP JP2003571244A patent/JP4430943B2/ja not_active Expired - Fee Related
- 2003-02-06 CN CN038044552A patent/CN1639113B/zh not_active Expired - Fee Related
- 2003-02-06 DK DK03742928T patent/DK1480945T3/da active
- 2003-02-06 AU AU2003215553A patent/AU2003215553B2/en not_active Ceased
- 2003-02-06 MX MXPA04007063A patent/MXPA04007063A/es active IP Right Grant
- 2003-02-06 BR BR0307533-8A patent/BR0307533A/pt not_active IP Right Cessation
- 2003-02-06 EP EP03742928A patent/EP1480945B1/de not_active Expired - Lifetime
- 2003-02-06 CA CA002476035A patent/CA2476035A1/en not_active Abandoned
- 2003-02-06 SI SI200330081T patent/SI1480945T1/sl unknown
- 2003-02-06 WO PCT/EP2003/001160 patent/WO2003072538A1/de active IP Right Grant
- 2003-02-06 KR KR1020047013247A patent/KR100934521B1/ko not_active IP Right Cessation
-
2004
- 2004-07-20 IL IL163111A patent/IL163111A/en not_active IP Right Cessation
- 2004-09-23 ZA ZA200407706A patent/ZA200407706B/en unknown
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2009
- 2009-09-29 JP JP2009224405A patent/JP5308297B2/ja not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010031027A (ja) * | 2002-02-26 | 2010-02-12 | Basf Se | 2−(クロロメチル)フェニル酢酸誘導体の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
SI1480945T1 (sl) | 2005-12-31 |
ATE304525T1 (de) | 2005-09-15 |
WO2003072538A1 (de) | 2003-09-04 |
EA200401013A1 (ru) | 2004-12-30 |
PL205226B1 (pl) | 2010-03-31 |
CA2476035A1 (en) | 2003-09-04 |
EA006653B1 (ru) | 2006-02-24 |
PL371057A1 (en) | 2005-06-13 |
CN1639113B (zh) | 2011-06-01 |
EP1480945B1 (de) | 2005-09-14 |
US7488840B2 (en) | 2009-02-10 |
AU2003215553A1 (en) | 2003-09-09 |
KR20040088543A (ko) | 2004-10-16 |
KR100934521B1 (ko) | 2009-12-29 |
ES2248762T3 (es) | 2006-03-16 |
JP2005518440A (ja) | 2005-06-23 |
BR0307533A (pt) | 2004-12-21 |
ZA200407706B (en) | 2006-06-28 |
JP2010031027A (ja) | 2010-02-12 |
IL163111A (en) | 2009-08-03 |
DK1480945T3 (da) | 2005-11-21 |
DE50301191D1 (de) | 2005-10-20 |
CN1639113A (zh) | 2005-07-13 |
MXPA04007063A (es) | 2004-10-29 |
EP1480945A1 (de) | 2004-12-01 |
JP5308297B2 (ja) | 2013-10-09 |
AU2003215553B2 (en) | 2009-05-28 |
US20050113597A1 (en) | 2005-05-26 |
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