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

HRID 2263366Notes

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.O>C(Cl)(Cl)(Cl)Cl>[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

Conditions

Temperature: 80 °C

Procedure

To a solution of 1 g of 4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester in 8 mL of carbon tetrachloride was added portionwise 0.1 g of benzoyl peroxide and 0.56 g of NBS. The resulting mixture was heated to 80° C. for 1.5 h. 0.1 g of NBS was added and the reaction mixture was heated to 80° C. overnight. An additional 0.1 g of NBS was added and the reaction mixture was heated to 80° C. for 2 h. It was then poured into water and extracted with dichloromethane. The organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (heptane 1/toluene 1 followed by pure toluene) to give 1.02 g of 4-bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester. 1 WO02067912

Workup

temperaturethe reaction mixture was heated to 80° C. overnight
temperaturethe reaction mixture was heated to 80° C. for 2 h
extractionextracted with dichloromethane
dry with materialThe organic extracts were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by column chromatography on silica gel (heptane 1/toluene 1 followed by pure toluene)

Sources & evidence

ORD record: ord-9212735b32d442d3ba1e37a576b6b1b0
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851493B2

Reaction notes

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