Benzoic acid, 4-fluoro-, ethyl ester → HCID 18376029, compound

Participants

Reaction Steps

To a solution of 3-cyano-6-methylpyridine (High Force Research Limited) (0.59 g 1,5 mmol) and ethyl 4-fluorobenzoate (0.84 g 5 mmol) (Aldrich) in dry THF (15 ml) stirring under nitrogen at −70° (Dricold/ethanol) was added dropwise lithium bis(trimethylsilyl)amide (10 ml M solution in hexane 10 mmol). The reaction was allowed to warm to room temperature, stirred under nitrogen for 20 hr, poured into water (200 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water (50 ml), brine (50 ml) and dried (MgSO4). Removal of solvent gave a solid which was crystallised from ethanol to give the title compound as a yellow solid (0.74 g 62%) which existed as a mixture of keto- and enol-forms by NMR. MH+: 241; mp: 170-1710 (uncorrected)

Provenance & Evidence