Boron tribromide → HCID 53754241, compound

Participants

Reaction Conditions

Reaction Steps

1,4-Bis-[3-(3-carbomethoxymethylphenyl)-(4-methoxy)phenyl]butane (0.9 g, 1.6 mmol) was dissolved in dichloromethane (3.0 mL), cooled in a dry ice bath, and treated with boron tribromide (1.2 mL, 12.8 mmol). The mixture was stirred at -78° C. for three hours then placed in a freezer at -10° C overnight. The reaction was quenched with ice water (10 mL) and extracted with dichloromethane (3×5 mL). The organic materials were combined, washed with water (25 mL), saturated sodium chloride (25 mL), dried (MgSO4) then concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 5:1 hexane/ethyl acetate) to give 1,4-bis-[3-(3-carbomethoxymethylphenyl)-4-hydroxyphenyl]butane (0.4 g, 47%). 1H NMR (400 MHz, CDCl3): 7.42 (d, J=7.4 Hz, 2H), 7.35-7.38 (m, 4H), 7.27-7.32 (m, 2H), 7.02-7.05 (m, 4H), 6.87 (d, J=8.0 Hz, 2H), 5.12 (s, 2H), 3.70 (s, 6H), 3.68 (s, 4H), 2.59 (m, 4H), 1.65 (m, 4H) ppm. IR (NaCl): 3439, 1732, 1606, 1263 cm-1.

Provenance & Evidence