Bromine → 5-tert-Butyl-2-methyl-4-thiocyanato-phenylamine

Participants

Reaction Conditions

Reaction Steps

A solution of 1.0 g (6.1 mmol) of 5-tert-butyl-2-methyl-phenylamine prepared in Example CCCC, sodium thiocyanide (1.62 g, 20.0 mmol) and MeOH (4.0 mL) was cooled to 0° C. and treated via addition funnel with a solution of bromine (0.35 mL, 6.7 mmol), sodium bromide (0.63 g, 6.13 mmol), and MeOH (5.0 mL). The mixture was stirred for 30 minutes and then carefully diluted with saturated sodium bicarbonate. The mixture was extracted with CH2Cl2 and the organic layers combined, dried (Na2SO4), and the solvent evaporated. The residue was then submitted to column chromatography (4:1 CH2Cl2 :hexanes to 19:1 CH2Cl2 :hexanes +1% MeOH) to provide the title compound. 1H NMR (CDCl3) δ 1.42 (s, 9 H), 2.09 (s, 3 H), 3.80 (bs, 2 H), 6.69 (s, 1 H), 7.35 (s, 1 H).

Provenance & Evidence