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

HRID 642298Notes

Reaction equation

HRID 642298 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ad7d1a9307284ef2a70717079befbd2b
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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