5-bromo-2-(methylsulfonylmethyl)aniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of {5-bromo-2-[(methylsulfonyl)methyl]phenyl}amine (Intermediate 74) (0.26 g) in chloroform (8 ml) was added potassium acetate (0.11 g) and acetic anhydride (0.195 ml). The mixture was heated under nitrogen at reflux for 18 h. 18-Crown-6 (0.26 g) and tert-butylnitrite (0.35 ml) were added and the mixture was stirred at reflux for a further 88 h. The mixture was concentrated under vacuum and the residue was purified by column chromatography on silica eluting with cyclohexane:ethylacetate (4:1 to 1:1) to give the title compound (0.14 g). The mixture was heated under nitrogen at reflux for 18 h at reflux for a further 88 h The mixture was concentrated under vacuum the residue was purified by column chromatography on silica eluting with cyclohexane:ethylacetate (4:1 to 1:1)