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

HRID 642298ノート

反応式

HRID 642298 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ad7d1a9307284ef2a70717079befbd2b
出典データセット
uspto-grants-2010_04
特許番号
US07696223B2

反応ノート

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