1-(Bromomethyl)-3-chlorobenzene → HCID 23130459, compound

Participants

Reaction Steps

n-Butyl lithium (2.6N hexane solution, 15.6 mL, 39 mmol) was added dropwise to a solution of 2-(5bromo-thiophen-2-yl)-[1,3]dioxolane (7.0 g, 30 mmol) in tetrahydrofuran (40 mL) at from −75° to −68° C., and the solution was stirred for 20 minutes. 3-Chlorobenzyl bromide (4.3 mL, 33 mmol) was added dropwise to this reaction solution at from −75° C. to −68° C., and the solution was stirred for 20 minutes. The cold bath was removed, and the reaction solution was gradually allowed to room temperature. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=20:1), and the title compound (1.6 g, 5.7 mmol, 19.0%) was obtained as a yellow oil.

Provenance & Evidence