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

HRID 18996

反応式

HRID 18996 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1cf7c89fa3a8465e90568a968c046442
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

関連ノート

読み込み中…