Boron tribromide → HCID 11633183, compound

Participants

Reaction Steps

Methyl ether (155) (0.14 g, 0.32 mmol) was treated with BBr3 in CH2Cl2 to give the crude product as a yellow viscous oil, which was purified by reverse phase preparation HPLC on Agilent 1100 to afford 69 mg (51%) of the title compound (156) as an off-white solid. mp 242-243° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.75-0.85 (m, 4H), 1.60-1.70 (m, 1H), 6.26 (d, J=15.9 Hz, 1H), 6.57 (d, J=8.6 Hz, 2H), 7.02 (dd, J1=9.0 Hz, J2=2.0 Hz, 1H), 7.12 (d, J=1.9 Hz, 1H), 7.16-7.28 (m, 6H), 7.34 (d, J=8.6 Hz, 2H), 7.52 (d, J=15.9 Hz, 1H), 7.58 (d, J=9.0 Hz, 1H). LCMS (APCI): m/z 423 (M+H)+, m/z 421 (M−H)−. Anal. Calc for C28H22O4.1.25H2O: C, 75.58; H, 5.55. Found: C, 75.34; H, 5.34.

Provenance & Evidence