Boron tribromide → HCID 11619024, compound

Participants

Reaction Steps

Methyl ether (163) (0.12 g, 0.27 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 95 mg (82%) of the title compound (164) as a white solid. mp 107-109° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.78 (t, J=7.4 Hz, 3H), 1.15-1.29 (m, 2H), 1.40-1.50 (m, 2H), 2.62 (t, J=7.9 Hz, 2H), 6.26 (d, J=15.9 Hz, 1H), 6.56 (d, J=8.8 Hz, 2H), 6.68 (d, J=8.4 Hz, 2H), 6.96 (d, J=8.6 Hz, 2H), 7.30-7.40 (m, 3H), 7.47 (t, J=7.9 Hz, 1H), 7.53 (d, J=15.9 Hz, 1H), 7.71 (s, 1H), 7.73 (d, J=8.5 Hz, 1H), 7.88 (d, J=8.2 Hz, 1H). LCMS (ESI): m/z 439 (M+H)+, m/z 437 (M−H)−. Anal. Calc for C29H26O4.⅙H2O: C, 78.89; H, 6.01. Found: C, 78.71; H, 5.91.

Provenance & Evidence