4-Fluorothiophenol → {2-[(4-Fluorophenyl)sulfanyl]ethyl}(methyl)amine

Participants

Reaction Steps

Reflux a mixture of (2-bromoethyl)methylamine hydrobromic acid salt (500 mg, 2.28 mmol), 4-fluorobenzenethiol (0.243 mL, 2.28 mmol), and potassium t-butoxide (512 mg, 4.56 mmol) in acetonitrile (10 mL) for 17 hours. Remove the solvent under vacuum and dissolve the residue in ether and 5 N sodium hydroxide solution. Extract the organic layer with 1 N hydrochloric acid solution. Neutralize the acidic aqueous layer with 5 N sodium hydroxide solution and extract twice with ether. Dry the combined ether extracts over magnesium sulfate and reduce under vacuum to give 260 mg of the titled compound as an oil.

Provenance & Evidence