Boron tribromide → HCID 15490888, compound

Participants

Reaction Steps

At -78° C., to a stirred solution of (2-benzyl-4,5-dimethylthiophen-3-yl)-(4-methoxy-3-isopropyl-phenyl)-methanone (6.48 g, 0.0178 mol) in CH2Cl2 (75 mL) was added dropwise boron tribromide (9.4 mL, 0.099 mol). After the addition was complete the dry ice/acetone bath was removed and the reaction was stirred for 2 h. The reaction was quenched into KH2PO4 (100 mL), extracted with CH2Cl2 and concentrated. Purification on silica gel, eluting with 5% EtOAc/pet. ether, gave 1.67 g (27%) of the title compound as a yellow solid. 1H NMR (DMSO-d6) β 9.49 (s, 1 H), 8.42 (s, 1 H), 7.94 (d, 1 H), 7.47-7.32 (m, 3 H), 7.01 (s, 1 H), 6.93 (s, 2 H), 3.32 (m, 1 H), 2.39 (s, 3 H), 1.59 (s, 3 H), 1.19 (d, 6 H).

Provenance & Evidence