Azobisisobutyronitrile → Ethyl 2-(bromomethyl)-3,6-dichlorobenzoate

HRID 577498ノート

反応式

HRID 577498 の反応式
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([C:10]([Cl:13])=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)Cl.ClCCl>[Br:15][CH2:14][C:3]1[C:2]([Cl:1])=[CH:12][CH:11]=[C:10]([Cl:13])[C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

参加物

6

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 86723723Ethyl 3,6-dichloro-2-methylbenzoate

生成物 1

HCID 86723724Ethyl 2-(bromomethyl)-3,6-dichlorobenzoate収率 100%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 3,6-dichloro-2-methylbenzoate (253b, 120 g, 0.52 mol) and N-bromosuccinimide (147 g, 0.82 mol) in chloroform (1 L) was treated with azobisisobutyronitrile (25.3 g, 0.15 mol) and the mixture refluxed overnight. After cooling to room temperature, the mixture was diluted with dichloromethane (800 mL) and washed with water (1.2 L). The aqueous layer was extracted with dichloromethane (800 mL). The combined organic extracts were washed with saturated aqueous sodium chloride solution (1.5 L), dried over sodium sulfate, and concentrated in vacuo to give ethyl 2-(bromomethyl)-3,6-dichlorobenzoate (253c, 160 g, 100% yield) which was used without further purification.

後処理

  1. temperaturethe mixture refluxed overnight
  2. washwashed with water (1.2 L)
  3. extractionThe aqueous layer was extracted with dichloromethane (800 mL)
  4. washThe combined organic extracts were washed with saturated aqueous sodium chloride solution (1.5 L)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3d86e46f619942e29e00f8256a694502
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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