Lithium Hydroxide → 3,3-Difluorocyclohexanecarboxylic acid

Participants

Reaction Steps

A 2 M aqueous solution of lithium hydroxide (26 mL) was added to a solution of methyl (1R,2R)-2-2-bromophenyl)-5,5-difluorocyclohexanecarboxylate (1.81 g, 5.46 mmol) in a mixture of methanol (20 mL) and THF (10 mL) with rapid stirring at room temperature for 15 hours. The reaction mixture was then diluted with water and extracted with ether prior to acidification to pH 2 with 2 M HCl followed by extraction with ethyl acetate (2×). The combined ethyl acetate extracts were washed with brine, dried (Na2SO4), and concentrated to afford (1R,2R)-2-2-bromophenyl)-5,5-difluorocyclohexanecarboxylic acid as a tan foam.

Provenance & Evidence