Methanol → 1-Bromo-2,5-dichloro-3-methoxybenzene

Participants

Reaction Steps

Methanol (5 mL) was added to potassium tert-butoxide (3.94 g, 123 mmol) suspended in toluene/DMPU (3:1, 240 mL), and the mixture was placed in an oil bath at 80° C. under N2 with a reflux condenser for 25 minutes to obtain a solution. The solution was then allowed to cool to room temperature under N2, after which 1-bromo-2,5-dichloro-3-fluorobenzene (10 g, 41 mmol) was added dropwise to the solution and the resulting suspension was placed in an oil bath at 80° C. under N2. After 4 hours, the reaction mixture was allowed to cool to room temperature and was then diluted with hexanes (200 mL) and water (100 mL). The layers were separated and the aqueous layer was extracted with hexanes (200 mL). The combined organic portions were washed with water (3×300 mL), dried (MgSO4), filtered and concentrated to give the title compound. 1H NMR (CDCl3) δ 7.20 (m, 1H), 6.80 (m, 1H), 3.90 (s, 3H).

Provenance & Evidence