Boron Trichloride → 4-Chloro-2,6-dimethoxyphenol

Participants

Reaction Steps

To a stirred solution 37a) (4.67 g, 23.1 mmol) in dry DCM (40 mL) at 0° C. under nitrogen was added BCl3 (1M in DCM, 24 mL, 24.0 mmol) drop-wise. The solution was allowed to warm to room temperature over 3.5 h. The reaction was quenched with the addition of H2O (40 mL) and the product extracted with EtOAc (3×30 mL). The organics were pooled, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, EtOAc/Petroleum Spirit, 2:8) to give the title compound as a white solid (4.29 g, 98%). 1H NMR (300 MHz, CDCl3) δ 6.58 (s, 2H), 5.41 (s, 1H), 3.88 (s, 6H), ESIMS m/z [M+H]+ 187.3.

Provenance & Evidence