Boron tribromide → (4-Hydroxyphenyl)(4-iodophenyl)methanone

Participants

Reaction Steps

To a solution of (4-iodo-phenyl)-(4-methoxy-phenyl)-methanone (1.7 g, 5 mmol in CH2Cl2 (20 mL) was added BBr3 (15 mL, 15 mmol; 1 M in CH2Cl2) at −78° C. The resulting mixture was allowed to warm to rt and stir at rt for 6 h. The mixture was poured onto 50 mL ice-water solution and extracted with CH2Cl2 (3×30 mL). The combined organic layers were washed with water (2×30 mL) and brine (20 mL) and dried over anhy. Na2SO4. The solvent was removed in vacuo to obtain the crude product which was purified by recrystallization from acetone-EtOAc-hexane to provide the title product (1.4 g, 85%) which was directly used for the next step.

Provenance & Evidence