Boron tribromide → 4-(4'-Hydroxyphenoxy)biphenyl

Participants

Reaction Conditions

Reaction Steps

4-(4-Methoxy-phenoxy)-biphenyl (1.0 g, 3.6 mmol) in anhydrous CH2Cl2 (10 mL) was cooled to −78° C. and 1M boron tribromide (10.8 mL, 10.8 mmol) in CH2Cl2 was added dropwise over period of 20 min under nitrogen. The resulting mixture was stirred at −78° C. for 2 h and at rt for 1 h. Then it was cooled to 0° C. and poured slowly over 1:1 mixture of CH2Cl2/water. CH2Cl2 layer was separated, washed with water, brine, dried over anhydrous MgSO4 and concentrated. The crude product was purified using silica gel flash chromatography (20% EtOAc/Hexane) to obtain the product as yellow solid (265 mg, 28%): MS; m/z 260.9 (M−H); 1H NMR (400 MHz, DMSO-d6); δ 6.79-6.82 (m, 1H), 6.91-6.98 (m, 2H), 7.30-7.49 (m, 4H), 7.60-7.68 (m, 6H), 8.36 (s, 1H).

Provenance & Evidence