Potassium Bromide → 2-Bromo-6-octylbenzo[d]thiazole

Participants

Reaction Conditions

Reaction Steps

To a solution of p-TsOH.H2O (108 mg, 0.57 mmol) in MeCN (2 mL) was added compound 6-octylbenzo[d]thiazol-2-amine (50 mg, 0.19 mmol). The resulting suspension was cooled to 10-15° C. and to this was added, gradually, a solution of NaNO2 (26 mg, 0.38 mmol) and KBr (56 mg, 0.48 mmol) in H2O (0.5 mL). The mixture was then stirred at r.t. for 1 h. Then the mixture was extracted with EtOAc and purified by silica gel chromatography using PE to give product the title compound (50 mg, 82%). 1H NMR (300 MHz, CDCl3) δ 7.880 (t, 1H), 7.585 (s, 1H), 7.286 (t, 1H), 2.711 (t, 2H), 1.686-1.571 (m, 2H), 1.309-1.186 (m, 10H), 0.874 (t, 3H).

Provenance & Evidence