Water → (E)-4-bromo-3-(2-chloro-phenoxy)-but-2-enoic acid ethyl ester

HRID 18996

반응식

HRID 18996 반응식
[CH2:1]([O:3][C:4](=[O:16])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])\[CH3:7])[CH3:2].[Br:17]N1C(=O)CCC1=O.O>ClCCl.N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N>[CH2:1]([O:3][C:4](=[O:16])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])\[CH2:7][Br:17])[CH3:2]

참가 물질

6

반응물 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 66894719(E)-3-(2-chloro-phenoxy)-but-2-enoic acid ethyl ester

생성물 1

HCID 66895331(E)-4-bromo-3-(2-chloro-phenoxy)-but-2-enoic acid ethyl ester수율 113%

시약·촉매·용매 2

HCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of (E)-3-(2-chloro-phenoxy)-but-2-enoic acid ethyl ester (1880 g, 7.82 mol) in dichloromethane (18.6 L) was added N-bromosuccinimide (1490 g, 8.29 mol) and 2,2′-azobis(2,4-dimethylvaleronitrile) (47 g, 0.188 mol) and the resulting solution heated to reflux for 23 h. The light yellow solution was cooled to room temperature and transferred to an extractor before water (19 L) was added. The biphasic mixture was stirred at room temperature for 1 h. The mixture was separated and the organic phase washed with a 20% sodium chloride solution (19 L). The solution was evaporated to give (E)-4-bromo-3-(2-chloro-phenoxy)-but-2-enoic acid ethyl ester (87.8% pure by HPLC, 2824 g, 99%) as a red oil.

후처리

  1. temperaturethe resulting solution heated
  2. temperatureto reflux for 23 h
  3. additionwas added
  4. customThe mixture was separated
  5. washthe organic phase washed with a 20% sodium chloride solution (19 L)
  6. customThe solution was evaporated

출처 및 근거

ORD 기록
ord-1cf7c89fa3a8465e90568a968c046442
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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