3-Bromo-4-hydroxyphenylacetic acid → 1-(2,4,6-Trihydroxyphenyl)-2-(3-bromo-4-hydroxyphenyl)ethanone

Participants

Reaction Steps

1,3.5-Trihydroxybenzaldehyde (1.01 g, 6.95 mmol) and 3-bromo-4-hydroxyphenylacetic acid (1.44 g, 6.25 mmol) were suspended in POCl3 (4 mL). After 1 min, an exothermic reaction occurred. The mixture was allowed to cool to room temperature. Zinc chloride (1M ether solution, 4.7 mmol) was added and the mixture was heated at 75° C. for 1 h. After cooling, the mixture was partitioned in ethyl acetate and 1 M aqueous HCl. The organic layer was washed with brine and dried with MgSO4. Purification on silica gel (MeOH/dichloromethane, gradient) afforded 1-(2,4,6-trihydroxyphenyl)-2-(3-bromo-4-hydroxyphenyl)ethanone (390 mg) as a tan solid.

Provenance & Evidence