Hydrochloric Acid → 6-Bromopyridine-2-carbaldehyde

Temperature

-78 °C

2,6-Dibromopyridine (25 g, 0.105 mol) is suspended in 200 ml of ether. The solution is cooled to -78° C. and n-butyllithium (65.6 ml, 1.6M, 0.105 mol) in hexane is added slowly dropwise over a 1.5 hour period. After 5 minutes, dimethylformamide (8.4 g, 0.115 mol) in 13 ml of ether is added slowly dropwise over one hour. The reaction is allowed to stir at -78° C. for 1.5 hours. The mixture is warmed to -25° C. and 40 ml of 6N hydrochloric acid is added. The mixture is allowed to warm to room temperature. The aqueous phase is extracted three times with ether and the combined organics are washed once with water, dried over sodium sulfate and evaporated. Trituration with pentane afforded 15.0 g of the title compound as a tannish-white solid.

1. temperatureThe mixture is warmed to -25° C.
2. temperatureto warm to room temperature
3. extractionThe aqueous phase is extracted three times with ether
4. washthe combined organics are washed once with water
5. dry with materialdried over sodium sulfate
6. customevaporated

ORD record

ord-82a1eeb6d9aa4393ad3389267ff0dcc1

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05116981