2-chloro-6-hydroxy-4-methoxybenzaldehyde

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-chloro-4,6-dimethoxybenzaldehyde [4] (3.15 g) in dichloromethane (30 mL) cooled at −78° C. was added boron tribromide (1M solution in dichloromethane, 16 mL). The mixture was stirred at −78° C. for 30 min, warmed and stirred at room temperature for 18 h. The mixture was cooled to 0° C., poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4. Evaporation of the solvent gave the title compound (2.85 g). 1H NMR (DMSO-d6): 12.15 (s, 1H), 10.14 (s, 1H), 6.74 (d, 1H, J=2.1 Hz), 6.53 (d, 1H, J=2.1 Hz), 3.86 (s, 3H). warmed stirred at room temperature for 18 h The mixture was cooled to 0° C. extracted with ethyl acetate The organic layer was washed with brine dried over MgSO4 Evaporation of the solvent