N-bromobutanimide → 4-Bromomethyl-2-(4-fluoro-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 642298노트

반응식

HRID 642298 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:18])=[O:5])[CH3:2].[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH2:18][Br:19])=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 9079430Ethyl 2-(4-Fluorophenyl)-4-methylthiazole-5-carboxylate

생성물 1

HCID 684283654-Bromomethyl-2-(4-fluoro-phenyl)-thiazole-5-carboxylic acid ethyl ester수율 94.1%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 2-(4-fluoro-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (1.95 g, 7.35 mmol), N-bromosuccinimide (1.37 g, 7.71 mol) and benzoyl peroxide (89 mg, 0.37 mmol) in carbon tetrachloride (20 mL) was refluxed for 16 h before it was cooled to room temperature and partitioned between dichloromethane and water. The organic layer was washed with saturated aqueous sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow oil (2.38 g); MS: (+) m/z 343.93, 345.96 (M+1, 79Br/81Br).

후처리

  1. temperaturewas refluxed for 16 h before it
  2. custompartitioned between dichloromethane and water
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ad7d1a9307284ef2a70717079befbd2b
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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