Methanesulfonyl chloride → (3-Phenylbenzo[b]thiophen-2-yl)methyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

Methanesulfonyl chloride (127 μL, 1.63 mmol) was added dropwise to a solution of (3-phenylbenzo[b]thiophen-2-yl)methanol (356 mg, 1.48 mmol) and DIPEA (322 μL, 1.85 mmol) in anhydrous DCM (10 mL) at 0° C. Stirring at 0° C. was continued for 15 min, then the mixture was slowly warmed to RT. After 2.5 h at RT, additional methanesulfonyl chloride (1 drop) was added and stirring was continued for 1 h. The reaction mixture was diluted with DCM and the organic fraction washed with water, dried (Na2SO4) and concentrated in vacuo affording the title compound as a yellow oil (408 mg, 87%). 1H NMR (DMSO-d6, 400 MHz): δ 8.07-8.02 (1H, m), 7.62-7.56 (2H, m), 7.55-7.37 (6H, m), 4.96 (2H, s), 3.33 (3H, s)

Provenance & Evidence