4-Fluorophenyl isothiocyanate → HCID 68488565, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethynyltrimethylsilane (0.89 g) in THF (15 mL) was added a 1.57M solution (5.0 mL) of n-butyllithium in hexane at −78° C. under a nitrogen atmosphere, and the mixture was stirred at the same temperature for 0.5 hours. After the reaction mixture was warmed to 0° C., a 4-fluorophenyl isothiocyanate (1.30 g) in THF (5 mL) was added dropwise thereto at −78° C. Then, the reaction mixture was slowly warmed to 0° C. At the same temperature, a solution of cyclohexylmethyl bromide (1.52 g) in THF (5 mL) was added dropwise thereto, and the mixture was stirred at 50° C. for 7 hours. The solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain cyclohexylmethyl N-(4-fluorophenyl)-3-(trimethylsilyl)thiopropionimidate (0.38 g) as a brown oil.

Provenance & Evidence