Dimethyl Disulfide → (2-Fluoro-3-methoxy-5-methylphenyl)(methyl)sulfane

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-fluoro-2-methoxy-4-methylbenzene (1.0 g) and THF (dry) (60 mL) was added sec-butyllithium (1.04 mol/L cyclohexane solution, 13.72 mL) dropwise over a period of 20 min at −78° C. After stirring at −78° C. for 20 min, to the mixture was added dimethyl disulfide (1.41 mL) at the same temperature. The mixture was stirred at −78° C. under argon atmosphere for 1 h. The mixture was quenched with saturated aqueous NH4Cl at −78° C. and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (1.34 g).

Provenance & Evidence