Sodium Chloride → 4-Formyl-3-methylbenzonitrile

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To a stirred solution of 4-bromo-3-methylbenzonitrile (4 g, 20 mmol) in tetrahydrofuran (100 ml), cooled to -100° C. under a nitrogen atmosphere, was added dropwise a solution of n-butyllithium in hexanes (1.6M, 12.8 ml). After addition, the pale red solution was stirred for 5 minutes at -100° C. and dry dimethylformamide (2.2 ml) then added dropwise. After 20 minutes, during which the temperature reached -60° C., the reaction mixture was poured onto a saturated solution of sodium chloride (100 ml). The organic phase was separated and combined with a diethyl ether (100 ml) wash of the aqueous phase, dried, filtered and evaporated. Crystallised from diethyl ether-hexane to give 4-cyano-2-methylbenzaldehyde as a white solid.

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