4-Fluorobenzyl chloride → HCID 13920588, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (-40° C.) solution of N-(1,1-dimethylethyl)-3-methyl-2-pyridinecarboxamide (38.4 g, 0.2 mole) in dry THF (250 mL) is added n-butyl lithium (185 mL, 0.44 mole). Then sodium bromide (1.9 g, 18 mmol.) is added and is allowed to stir for 15 minutes. 4-Fluorobenzylchloride (31.8 g. 0.22 mole) was added and the reaction is allowed to stir for 21/2 hours while warming up to -5° C. The reaction is then quenched with water and the product is extracted twice with ethyl acetate followed by washing twice with brine. The organic phase is dried over Na2SO4, filtered and solvent is removed to give desired compound (60.0 g) in 99% yield, m.p. 59°-61° C.

Provenance & Evidence