Benzoyl chloride → HCID 80073716, compound

Participants

Reaction Steps

To a cooled suspension of AlCl3 (150 mg, 1.2 eq) in 2 mL of anhydrous DCM at 0° C., was added dropwise benzoyl chloride (120 μL, 1.1 eq). Once the mixture was become limpid (15 min), 1-bromo-3,5-dimethoxybenzene (208 mg, 0.958 mmol) solubilized in 1 mL of DCM was slowly added at 0° C. After 1 h15 of stirring at low temperature, the yellow reaction mixture was hydrolyzed with a saturated NH4Cl solution (6 mL) The aqueous layer, more diluted with water and with a saturated NaHCO3 solution, was extracted with DCM (3×12 mL) The combined extracts were washed with aq. NaHCO3 solution (20 mL), with brine (20 mL), dried over MgSO4 and solvents were removed in vacuo. The crude was purified by silica gel flash chromatography (cyclohexane/AcOEt 100:0 to 93:7) and allowed to isolate (2-bromo-4,6-dimethoxyphenyl)(phenyl)methanone (264 mg) and (4-bromo-2,6-dimethoxyphenyl)(phenyl)methanone (29.4 mg) in 95% chemical yield (90/10 ratio) as white solids. 1H NMR (300 MHz, CDCl3) δ 7.82 (d, J=8.5 Hz, 2H), 7.56 (t, J=7.4 Hz, 1H), 7.43 (t, J=7.5 Hz, 2H), 6.79 (s, 2H), 3.70 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 194.4 (C═O), 158.1 (C), 137.4 (C), 133.6 (CH), 129.5 (2CH), 128.6 (2CH), 124.2 (C), 116.9 (C), 108.0 (2CH), 56.3 (2OCH3); MS (ESI) m/z: 321.0, 322.9 [M+H, 79Br, 81Br]+; 243.1, 244.9 [M-Ph, 79Br, 81Br]+.

Provenance & Evidence