Boron tribromide → HCID 20765600, compound

Participants

Reaction Steps

Boron tribromide (84 mL of a 1.0M solution in CH2Cl2) was added to a suspension of Example 310C in CH2Cl2 (85 mL) at 0° C. After addition was completed, the ice-water bath was removed, and the homogeneous dark solution was stirred for 2 hours before the mixture was poured into 1 N aqueous HCl (100 mL) and ice (100 g), and extracted with EtOAc (3×100 mL). ). The organic layers were combined, washed with brine (1×50 mL), dried (MgSO4), filtered, and concentrated to a white solid (11.3 g). 1H NMR (DMSO-d6, 300 MHz) δ 10.26 (s, 1H), 7.82 (d, J15.6, 1H), 7.74 (d, J=8.5 Hz, 1H), 7.44 (dt, J=7.8 Hz, J=1.7 Hz, 1H), 7.41 (dd, J=7.4 Hz, J=1.7 Hz, 1H), 7.05 (dd, J=8.4 Hz, J=1.3 Hz, 1H), 6.94 (dt, J=7.8 Hz, J=1.4 Hz, 1H), 6.52 (d, J=8.2 Hz, 1H), 6.50 (d, J=16.0 Hz, 1H); MS (APCI) m/z 339 (M−H)−, 375 (M+Cl)−.

Provenance & Evidence