Boron tribromide → HCID 25030037, compound

Participants

Reaction Conditions

Reaction Steps

Ketone 17 was dissolved in dry DCM and the resulting solution was cooled to −78° C. BBr3 (1.5 eq, 0.49 mM) was then added drop wise and the reaction mixture was allowed to warm to room temperature and was stirred for an additional 12 hours. After the completion of the reaction as determined by TLC, the reaction mixture was diluted with methanol, and then washed with bicrab, water brine. The product was then subjected to column chromatography using 20% EtOAc/hexanes as the solvent system. Yield=46.5% (Rf=0.31; 20% EtOAc/Hexanes) 1H NMR, 300 MHz Varian, CDCl3 δ 7.88 (d, J=8.4 Hz, 2H), 7.59 (t, J=7.2 Hz, 1H), 7.54 (d, J=7.5 Hz, 1H), 7.47 (m, 2H), 7.43 (d, J=6.3 Hz, 2H), 7.38 (s, 1H), 7.34 (s 7.27 (m, 1H), 2.46 (s, 3H), MS: m/z (ESI, pos.)=325.5 ([M+23]). HPLC retention time: 11.246 min. and 10.804 min; purity 97.92%.

Provenance & Evidence