Boron tribromide → HCID 86760088, compound

Participants

Reaction Steps

A mixture of 1.44 g (2.84 mmol) of ethyl (E)-4-[3-(1-adamantyl)-4-benzyloxyphenyl]-3-methylcinnamate was stirred in 10 ml of CH2Cl2 at −78° C. under Ar while 8.0 ml of 1.0 M BBr3 in CH2Cl2 was added slowly over a period of 0.5 hour. The reaction mixture was stirred for 2 hours more, at which time the reaction was complete. The mixture was extracted with EtOAc, washed with brine and water, dried (MgSO4), filtered, and concentrated. Flash column chromatography (20% EtOAc/hexane) yielded a pale-yellow solid (0.86 g, 73%: m.p. 193-195° C.; Rf0.47 (20% EtOAc/hexane); 1H NMR (300 MHz, CDCl3) δ 1.78, 2.14 (2 s, 12, AdCH2), 2.09 (s, 3, AdCH), 1.35 (t, J=7.2 Hz, 3 CH3), 2.31 (s, 3, ArCH3), 4.27 (q, J=7.6 Hz, 2, CH2), 4.94 (s, 1, OH), 6.46 (d, J=16.4 Hz, 1, HC═CCO), 6.71 (d, J=8.4 Hz, 1, ArH), 7.03 (dd, J=8.4, 1.6 Hz, 1, ArH), 7.16 (d, J=2.8 Hz, 1, ArH), 7.25 (s, 1, ArH), 7.39 (dd, J=9.2, 2.4 Hz, 1, ArH), 7.41 (s, 1, ArH), 7.71 ppm (d, J=16.0 Hz, 1, C═CHCO).

Provenance & Evidence