Benzoyl Peroxide → 4-Bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic Acid Ethyl Ester

HRID 1172668Notes

Reaction equation

HRID 1172668 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:21])=[O:5])[CH3:2].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:47])C(=O)C1>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:21][Br:47])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27372104-Methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 179517684-Bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 200 g of commercially available 4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester in 1.6 L of dichloromethane were added 20.5 g of benzoyl peroxide and 124 g of NBS. The resulting mixture was refluxed in the dark for 22 h. After cooling to 0° C., the mixture was filtered. The filtrate was concentrated to half volume under reduced pressure, washed with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give a white solid. The solid was recrystallized in 900 mL of diisopropyl ether 80/dichloromethane 20 to give a first crop of 101 g of 4-bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester. The filtrate was concentrated under reduced pressure then recrystallized in 300 mL of diisopropyl ether 90/dichloromethane 10 to give a second crop of 72 g. A total of 173 g of 4-bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester was obtained as a white solid. 4 WO02067912

Workup

  1. temperatureThe resulting mixture was refluxed in the dark for 22 h
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrate was concentrated to half volume under reduced pressure
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a white solid
  9. customThe solid was recrystallized in 900 mL of diisopropyl ether 80/dichloromethane 20

Sources & evidence

ORD record
ord-527ddc55159f4317af6a3a58e6721982
Source dataset
uspto-grants-2010_11
Patent number
US07834030B2

Reaction notes

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