Boron tribromide → HCID 11582975, compound

Participants

Reaction Steps

Methyl ether (108) (0.15 g, 0.33 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 99 mg (68%) of the title compound (109) as pale yellow solid. mp 126-128° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.72 (d, J=6.6 Hz, 6H), 1.55-1.65 (m, 1H), 2.47 (d, J=7.1 Hz, 2H), 6.26 (d, J=15.9 Hz, 1H), 6.55 (d, J=8.8 Hz, 2H), 6.96 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.10-7.16 (m, 3H), 7.17-7.27 (m, 3H), 7.34 (d, J=8.8 Hz, 2H), 7.47 (s, 1H), 7.51 (d, J=15.9 Hz, 1H), 7.60 (d, J=9.0 Hz, 1H). LCMS (ESI): m/z 439 (M+H)+, m/z 437 (M−H)−. Anal. Calc for C29H26O4.0.25H2O: C, 78.62; H, 6.03. Found: C, 78.45; H, 5.96.

Provenance & Evidence