Boron tribromide → HCID 11561520, compound

Participants

Reaction Steps

Methyl ether (116) (0.15 g, 0.32 mmol) was treated with BBr3 in CH2Cl2 to give the crude product as orange viscous oil, which was purified by reverse phase preparation HPLC on Agilent 1100 to afford 79 mg (54%) of the title compound (117) as a light yellow solid. mp 110-113° C. 1H NMR (400 MHz, CH3OH-d4): δ 0.77 (t, J=6.8 Hz, 3H), 1.05-1.20 (m, 4H), 1.35-1.50 (m, 2H), 2.54 (t, J=7.8 Hz, 2H), 6.25 (d, J=16.0 Hz, 1H), 6.55 (d, J=8.8 Hz, 2H), 6.96 (dd, J1=9.0 Hz, J2=2.2 Hz, 1H), 7.08-7.15 (m, 3H), 7.17-7.27 (m, 3H), 7.33 (d, J=8.8 Hz, 2H), 7.48-7.57 (m, 2H), 7.59 (d, J=9.2 Hz, 1H). LCMS (ESI): m/z 451 (M−H)−. Anal. Calc for C30H28O4.0.25H2O: C, 78.84; H, 6.29. Found: C, 78.80; H, 6.14.

Provenance & Evidence