Methanesulfonic Acid → 1-Bromo-4-chloro-5-(4-ethylbenzyl)-2-methoxybenzene

Participants

Reaction Steps

(5-bromo-2-chloro-4-methoxyphenyl)(4-ethylphenyl)methanone (21) (5.6 g, 69%) was dissolved in trifluoroacetic acid (40 mL). To this mixture was added triethylsilane (6.3 mL, 40 mmol) and methanesulfonic acid (0.40 mL, 6.0 mmol). The resulting solution was stirred at room temperature for 2.5 hours, after which it was partitioned between water and ethyl acetate. The organic layer was washed with water (1×25 mL), followed by saturated NaHCO3 (2×25 mL) and brine (25 mL). The organic layer was dried (Na2SO4), filtered, and evaporated. Silica gel chromatography with 0-10% ethyl acetate in hexane gave the title compound (4.7 g, 88%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.29 (s, 1H), 7.09-7.04 (m, 4H), 6.88 (s, 1H), 3.95 (s, 2H), 3.84 (s, 3H), 2.61 (q, J=7.5 Hz, 2H), 1.21 (t, J=7.5 Hz, 3H).

Provenance & Evidence