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

HRID 577498노트

반응식

HRID 577498 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d86e46f619942e29e00f8256a694502
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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