Boron tribromide → HCID 118013407, compound

Participants

Reaction Steps

A solution of BBr3 (9.0 mmol, 1M in CH2Cl2) was added dropwise to a solution of 10 (1.8 mmol) in dry CH2Cl2 (4.0 mL) under N2 at −78° C. The reaction mixture was stirred at this temperature for 1 h. After this period, the reaction was allowed to warm to room temperature and stirred for 12 h. After reaction completion, the solution was quenched with methanol, and concentrated in vacuo. The residue was extracted with CH2Cl2 and washed with a solution of NaHCO3. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give (E)-3-(3-chloro-5-(2-hydroxyphenoxy)phenyl)acrylonitrile (11) (0.14 g, 51%) 1H NMR (400 MHz, CDCl3) δ 7.29 (s, 1H), 7.21-7.10 (m, 2H), 7.11-7.01 (m, 2H), 6.92 (ddt, J=16.0, 14.5, 4.9 Hz, 3H), 5.85 (dd, J=16.6, 5.2 Hz, 1H), 5.51 (s, 1H).

Provenance & Evidence