1-Octanethiol → Benzenepropanoic acid, alpha,alpha-difluoro-4-hydroxy-, ethyl ester

Participants

Reaction Steps

To a solution of ethyl 2,2-difluoro-3-(4-methoxyphenyl)propanoate (1.72 g, 7.05 mmol) synthesized according to the method described in Synthesis, vol. 13, pages 1917-1924, 2000 and aluminum chloride (2.82 g, 21.2 mmol) in dichloromethane (50 mL) was added dropwise 1-octanethiol (2.06 g, 14.1 mmol) and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was poured into ice water and stirred for 30 min. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=8:92-60:40) to give the title compound (0.90 g, yield 56%) as a colorless oil.

Provenance & Evidence