Water → HCID 86721879, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-chloro-benzyl)-N-isobutyl-4-methoxy-benzenesulfonamide (1.03 g, 2.8 mmol) in DCM (25 mL) was added tetrabutylammonium iodide (1.14 g, 3.1 mmol) and the reaction was cool to −78° C. To the solution was added boron trichloride (4.2 mL, 4.2 mmol of 1 M solution in DCM) over 2 minutes then stirred for a further 5 minutes. The reaction was left to warm to 0° C. and stirred for further 2 hours. Water and saturated aqueous NaHCO3 were added, extracted with DCM, filtered through a phase separator, concentrated then purified by silica gel column chromatography (0-30% EtOAc in cyclohexane) to give N-(4-chloro-benzyl)-4-hydroxy-N-isobutyl-benzenesulfonamide (629 mg, 64%). LCMS (m/z, Method A) ES− 352 [M−1]−.

Provenance & Evidence