N-bromobutanimide → Methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoate

HRID 2121178노트

반응식

HRID 2121178 반응식
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[O:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:20])=[CH:6][C:5]=1[O:11][S:12]([C:15]([F:17])([F:16])[F:18])(=[O:14])=[O:13]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 18474576Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate

생성물 1

HCID 18474595Methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoate수율 80.2%

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

To a stirred solution of 2-(trifluoromethanesulfonyloxy)-4-methylbenzoic acid methyl ester (19.6 g, 65.8 mmol), prepared as in Example 204A, in 250 mL CCl4 was added N-bromosuccinimide (12.29 g, 69.1 mmol) followed by 2,2′-azobisisobutyronitrile (108 mg, 0.658 mmol) and the reaction was heated to reflux. After 16 hours, the reaction was evaporated and the residue was purified by flash chromatography over silica gel (10% ethyl acetate-hexanes) to give 19.9 g (80%) of 2-(trifluoromethanesulfonyloxy)-4-bromomethylbenzoic acid methyl ester as a yellow oil.

후처리

  1. temperaturethe reaction was heated to reflux
  2. customthe reaction was evaporated
  3. customthe residue was purified by flash chromatography over silica gel (10% ethyl acetate-hexanes)

출처 및 근거

ORD 기록
ord-021253110724429d8d88c46e39a6e0e1
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693123B2

반응 노트

불러오는 중…