Hydrochloric Acid → HCID 58495647, compound

Participants

Reaction Steps

Dissolve sodium metal (343 mg, 14.9 mmoles) in anhydrous ethanol (20 mL) at room temperature under nitrogen atmosphere. Then add cyclohexyl mercaptan (2 mL, 16.37 mmoles) and stir at room temperature for 30 min. Add then neat 4-fluoro-benzonitrile (1.8 g, 14.9 mmol) and heat the resulting solution at 80° C. overnight. Cool the reaction to room temperature and quench the reaction by adding 1N aqueous HCl (100 mL). Concentrate the mixture in vacuo and take up the residue with EtOAc (100 mL). Wash the organic layer with saturated aqueous NaHCO3 (100 mL) and brine (100 mL). Dry the organic phase over MgSO4 and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel (120 g, pre-packed cartridge) eluting with cyclohexane/EtOAc (98:2 to 80:20 gradient) to afford the desired intermediate (2.2 g, 68%). GC-MS m/z: 217 (M+).

Provenance & Evidence