4-Fluorobenzyl chloride → HCID 13920588, compound

Participants

Reaction Conditions

Reaction Steps

Cool a solution of N-(1,1-dimethylethyl)-3-methyl-2-pyridinecarboxamide (38.4 g, 0.2 mole) in dry THF (250 mL) to -40-° C. and add n-butyl lithium (185 mL, 0.44 mole). Add sodium bromide (1.9 g, 18 mmol.) and stir for 15 minutes. Add 4-fluorobenzylchloride (31.8 g. 0.22 mole) and stir for 2.5 hours while warming to -5° C. Quench the reaction with water and extract the product twice with ethyl acetate, then wash with brine (2×). Dry the organic phase over Na2SO4, filter and remove the solvent to give the title compound. (60.0 g, Yield 99%, m.p. 59°-61° C.)

Provenance & Evidence