反应详情

温度

-100 °C

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.

1. additionAfter addition
2. waitAfter 20 minutes
3. customreached -60° C.
4. customThe organic phase was separated
5. washwash of the aqueous phase
6. customdried
7. filtrationfiltered
8. customevaporated
9. customCrystallised from diethyl ether-hexane