Benzonitrile, 3-(bromomethyl)- → 3-(2-(7-Chloroquinolin-2-yl)ethyl)benzonitrile

Participants

Reaction Steps

To a solution of 7-chloroquinaldine (17.7 g) in THF (80 mL) at -78° was added a solution of 100 mL lithium diisopropylamide (LDA) (1M) dropwise. After addition the solution was warmed to -20° and added dropwise to 3-cyanobenzyl bromide (20 g) in THF (80 mL) at 0°. The reaction mixture was stirred 1 hr at 0° and warmed to room temperature (30 min). The mixture was partitioned between pH 7 buffer (25% NH4OAc) and ethyl acetate. The organic layer was dried and evaporated. Flash chromatography of the residue using 30% ether in hexane afforded the title compound.

Provenance & Evidence