Sodium Hydroxide → 1-Bromo-3-(methanesulfonyl)-5-methylbenzene

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dibromotoluene (2.0 g, 8.0 mmol), sodium methanesulfinate (0.92 g, 9.0 mmol), copper(I) iodide (152 mg, 0.8 mmol), proline (0.18 g, 1.6 mmol) and sodium hydroxide (64 mg, 16 mmol) in DSMO (15 mL, anhyd) was heated in a microwave unit (Biotage Initiator™) at 210° C. for 20 min. The reaction was repeated two more times and the reaction mixtures were combined, diluted with H2O and extracted with EtOAc. The combined extracts were washed with H2O and brine, then dried (Na2SO4), concentrated and purified by chromatography (silica, EtOAc/Hex, 0:100 to 40:60) to give the title compound (1.2 g, 20% combined yield) as a white solid. GC-MS (EI): 248, 250.

Provenance & Evidence