Bromine → ethyl 1-({5-methyl-4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

Participants

Reaction Steps

Under a nitrogen atmosphere, to a solution (10 mL) of 1-[3-(trifluoromethyl)phenyl]propan-1-one (1.0 g, 4.95 mmol) in diethyl ether was added bromine (0.15 mL, 5.94 mmol) at 0° C., and the mixture was stirred at room temperature overnight. An aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in ethanol (4 mL), the compound (175 mg, 0.82 mmol) obtained in Example 1b was added and the mixture was heated under reflux for 3 hr. The reaction mixture was allowed to cool and the solvent was evaporated under reduced pressure. The obtained crude product was purified by recrystallization (ethyl acetate-hexane) to give the title compound (112 mg, 35%) as colorless crystals.

Provenance & Evidence