Triethylamine → (4-(5-Bromo-2-chlorobenzyl)phenoxy)(tert-butyl)dimethylsilane

Participants

Reaction Steps

To a stirred suspension of 4-(5-bromo-2-chlorobenzyl)phenol (60 g, 0.202 mol) and tert-butylchlorodimethylsilane (37.9 g, 0.252 mol) in acetonitrile (300 mL) was added dropwise triethylamine (54.4 mL, 0.390 mol) so that the reaction temperature did not exceed 5° C. After the addition was completed, the reaction mixture was stirred for 2 hours at 10˜15° C. This reaction mixture was filtered, and the filter cake was washed with petroleum ether (2×50 mL). The combined organic layers were evaporated under reduced pressure (30° C.), and the residue was dissolved in petroleum ether (300 mL). The solution was washed with water (100 mL×2) and evaporated, and the residue was dissolved in ethanol (180 mL) at 35° C. with stirring. This solution was cooled to 5˜10° C. and kept for 4 h. The solids were filtered, the filter cake was washed with cold ethanol (0˜5° C., 60 mL) and then dried under vacuum at 25° C. overnight to give 22f as a white solid (72 g, 86.6% yield; HPLC purity 99%, retention time 6.6 min). 1H-NMR (CDCl3, 400 MHz): δ 7.21˜7.28 (m, 3H), 7.06 (d, J=8.0 Hz, 2H), 6.82 (d, J=8.0 Hz, 2H), 4.00 (s, 2H), 1.00 (s, 9H), 0.21 (s, 6H); MS ESI (m/z) 411 [M+1]+, calc. 410.

Provenance & Evidence