Water → HCID 86731581, compound

Participants

Reaction Conditions

Reaction Steps

N-(2,4-dimethylphenyl)-N-isobutyl-3-methoxybenzenesulfonamide (431.4 mg, 1.242 mmol) was dissolved in dichloromethane (DCM) (10 mL) and cooled to −78° C. BBr3 in DCM (1M) (6.21 mL, 6.21 mmol) was added dropwise and the reaction put under nitrogen. The reaction was allowed to reach room temperature and left to stir overnight. Water (20 mL) was added dropwise into the reaction mixture, until no more fumes were released. The crude product was then extracted to the organic phase of an aqueous work up between DCM (30 mL) and water (20 mL). The aqueous phase was washed twice with DCM (20 mL×2). The organic phase was then dried and concentrated in vacuo. The crude product was then dissolved in a minimum of DCM, and loaded onto a silica column before being purified by silica column chromatography (20 mins, 20 g, 0-25% EtOAc in cyclohexane). The relevant fractions were then combined and condensed, to give the product, N-(2,4-dimethylphenyl)-3-hydroxy-N-isobutylbenzenesulfonamide, 384.4 mg.

Provenance & Evidence