Dichloromethane → 3-Fluoro-4-(2-phenylethoxy)cyclohexyl methanesulfonate

Participants

Reaction Steps

A methylene chloride (10 mL) solution of 3-Fluoro-4-(2-phenylethoxy)cyclohexanol (0.450 g, 1.89 mmol) in N,N-diisopropylethylamine (0.688 mL, 3.96 mmol) was cooled in an ice bath under nitrogen. Methanesulfonyl chloride (0.154 mL, 1.98 mmol) was added dropwise to the reaction solution. After 0.5 h the contents of the reaction flask were washed with 5% potassium bisulfate. The aqueous layer was extracted (2×) with methylene chloride and the combined organic portions dried with anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. Flash column chromatography (hexane:ethyl acetate, 60:40) gave 3-Fluoro-4-(2-phenylethoxy)cyclohexyl methanesulfonate as a colorless oil (0.597 g, 100% yield).

Provenance & Evidence