Triethylamine → 3-(4-Bromo-3,5-dimethylphenyl)propyl methanesulfonate

Participants

Reaction Steps

To a cooled (0° C.) solution of 3-(4-bromo-3,5-dimethylphenyl)propan-1-ol (250 mg) and triethylamine (160 μL) in dichloromethane (2 mL) is added methanesulfonyl chloride (850 μL). The mixture is stirred for 12 hours at room temperature. The mixture is partitioned between dichloromethane and saturated aqueous NaHCO3 solution and stirred vigorously for 30 minutes. The organic phase is separated, washed with brine and dried (MgSO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→50:50) to give the title compound. Yield: 235 mg; LC (method 8): tR=0.44 min; Mass spectrum (ESI+): m/z=343 [M+Na]+.

Provenance & Evidence