Boron tribromide → HCID 58828406, compound

Participants

Reaction Steps

The product of step 1 (1.07 g, 4.75 mmol) was taken up in a 1 M methylene chloride solution of boron tribromide (20 mL, 20 mmol). After heating at reflux overnight the reaction was quenched by the dropwise addition of methanol (ca., 5 mL), and briefly refluxed. The mixture was then concentrated and the residue partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was dried (sodium sulfate) and concentrated to afford crude product as a brown solid. Flash chromatography over silica (hexanes/ethyl acetate) afforded 0.891 g (89%) of product a as a near colorless, crystalline solid: 1H NMR (CDCl3) δ 7.42 (t, J=7.7 Hz, 2H), 7.32 (dd, J=8.3, 1.8 Hz, 1H), 7.23 (t, J=7.4 Hz, 1H), 7.12-7.01 (m, 4H), 6.29 (s, 1H) ppm.

Provenance & Evidence