Boron tribromide → HCID 11719093, compound

Participants

Reaction Steps

Methyl ether 84 (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 95 mg (65%) of the title compound (85) as pale yellow solid. mp 128-130° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.74 (t, J=7.3 Hz, 3H), 1.10-1.25 (m, 2H), 1.35-1.45 (m, 2H), 2.50-2.60 (m, 2H), 6.25 (d, J=16.1 Hz, 1H), 6.55 (d, J=8.6 Hz, 2H), 6.96 (dd, J1=9.0 Hz, J2=2.0 Hz, 1H), 7.08-7.18 (m, 3H), 7.18-7.28 (m, 3H), 7.33 (d, J=8.6 Hz, 2H), 7.46-7.58 (m, 2H), 7.59 (d, J=9.0 Hz, 1H). LCMS (ESI): m/z 439 (M+H)+, m/z 437 (M−H)−. Anal. Calc for C29H26O4.0.4H2O: C, 78.15; H, 6.06. Found: C, 78.03; H, 6.00.

Provenance & Evidence