Boron tribromide → HCID 11517461, compound

Participants

Reaction Steps

Methyl ether (100) (0.15 g, 0.34 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 96 mg (66%) of the title compound (101) as pale yellow solid. mp 120-122° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.77 (t, J=7.4 Hz, 3H), 1.45-1.55 (m, 2H), 2.52 (t, J=7.8 Hz, 2H), 6.25 (d, J=15.9 Hz, 1H), 6.55 (d, J=8.7 Hz, 2H), 6.96 (dd, J1=9.0 Hz, J2=2.4 Hz, 1H), 7.10-7.16 (m, 3H), 7.18-7.27 (m, 3H), 7.34 (d, J=8.8 Hz, 2H), 7.48-7.56 (m, 2H), 7.69 (d, J=9.0 Hz, 1H). LCMS (ESI): m/z 425 (M+H)+, m/z 423 (M−H)−. Anal. Calc for C28H24O4.0.33H2O: C, 78.12; H, 5.78. Found: C, 77.97; H, 5.58.

Provenance & Evidence