Methanol → N-(3-Bromophenethyl)-4-methylbenzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

TsCl (11 g, 57.5 mmol, 1.15 eq.) was dissolved in DCM (150 mL) and cooled to 0° C. To this solution was added a solution of 3-bromo-phenethyamine (10 g, 50 mmol) in DCM (50 mL), followed by Et3N (18 mL). The solution was stirred at r.t. overnight when TLC (5% MeOH in DCM) showed that the reaction was complete. LCMS: t=4.158, MS 354/356. 3 g of polymer-supported-amine was added, stirred for 1 h at r.t. The solution was filtered through a Celite pad, rinsed with DCM and the solvent was evaporated to dryness, re-dissolved in DCM (100 mL) and water (20 mL). The two layers were separated, and the aqueous layer was extracted with DCM (20 mL×2). The combined DCM extracts were washed with 1N H3PO4 (2×20 mL) and sodium bicarbonate (20 mL), and brine (15 mL×2), dried (anhydrous potassium carbonate), filtered, and concentrated in vacuo. The crude product was purified on a silica gel column, eluted with DCM (TLC: DCM) to get 17.89 g (100%) of the title compound as a off-white solid, on standing.

Provenance & Evidence