Boron tribromide → HCID 66869566, compound

Participants

Reaction Conditions

Reaction Steps

(2-Chloro-7-methoxy-naphthalen-1-yl)-acetic acid ethyl ester (12.0 g, 43.10 mmol) and tetrabutylammonium iodide (20.7 g, 56.04 mmol) are dissolved under an atmosphere of argon in CH2Cl2 (240 ml). The reaction mixture is cooled to −78° C. and a 1 M solution of BBr3 in CH2Cl2 (108 ml, 107.77 mmol) is added during 30 minutes. After stirring at −78° C. for 15 minutes and at RT for 1 h, TLC analysis indicates complete consumption of starting material. A sat. aqueous solution of NaHCO3 (8 ml) is carefully added. The organic layer is separated, washed with brine, dried over Na2SO4 and concentrated. Purification by FCC (hexane/EtOAc 4:1 to 3:2) yields the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.51 (t, J=9.9 Hz, 3H), 4.43 (q, J=9.9 Hz, 2H), 4.48 (s, 2H), 6.28-6.36 (br, 1H), 7.29-7.32 (m, 1H), 7.48-7.49 (m, 1H), 7.58 (d, J=10 Hz, 1H), 7.89 (d, J=10 Hz, 1H), 7.96 (d, J=10 Hz, 1H). ES+−MS: 265.2, 267.2 [M+H]+.

Provenance & Evidence