1-Octanol → 1-Fluorooctane

Participants

Reaction Steps

A solution of 13.0 g (0.1 mole) of 1-octanol in 25 ml of methylene chloride was added dropwise to a solution of 16.1 g (0.1 mole) of diethylaminosulfur trifluoride in 60 ml methylene chloride cooled to -70° to -65°. The reaction mixture was then warmed to 25° and 50 ml of water was added. The lower organic layer was separated, dried (MgSO4) and then distilled to give 12.0 g (90%) of 1-fluorooctane as a colorless liquid: bp 42°-43° (20 mm), 19F nmr (CCl3F) δ -218.8 ppm (t, t, 1F, J = 49, 25 Hz).

Provenance & Evidence