Hydrochloric Acid → HCID 18424393, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-4-chlorobenzotrifluoride (1.50 g), 1-fluoro-2-fluoromethyl-3-buten-2-ol (0.80 g), potassium carbonate (2.10 g), tetrabutylammonium bromide (325 mg), palladium acetate (56 mg) and N,N-dimethylacetamide (10 ml) was stirred under a nitrogen atmosphere at 80° C. for 14 hours. To the reaction mixture, 1 N HCl was added followed by extraction with a hexane/ethyl acetate mixed (1/1) solvent; the resulting organic layers were combined and washed with a saturated aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride; the mixture was dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluent; hexane/ethyl acetate=10/1) to give 4-(2-chloro-5-trifluoromethylphenyl)-1-fluoro-2-fluoromethyl-3-trans-buten-2-ol (1.53 g) having a melting point of 61-62° C.

Provenance & Evidence