Carbon Dioxide → 6-Bromopyridine-2-carboxylic acid

Temperature

-50 °C

A suspension of 2,6-dibromopyridine (19 g) in diethylether (200 ml) was added to a mixture of n-butyl lithium (130 ml of a 1.6M solution in hexane) and diethylether (200 ml) cooled to -50° C. The resulting solution was stirred at -50° C. for 10 minutes before pouring onto a slurry of diethyl ether(100 ml) and dry-ice. The mixture was allowed to warm to room temperature and filtered. The resulting solid was dissolved in 2N sodium hydroxide (350 ml) and extracted with diethyl ether (2×300 ml). The aqueous layer was separated and acidified with 2N hydrochloric acid. The resulting precipitate was filtered and washed with water to give 6-bromo-2-pyridine carboxylic acid (7.25 g): NMR (d6DMSO) δ7.69(d,1H), 7.95(d,1H), 8.05(dd,1H); m/e 202(M+H)+.

1. temperatureto warm to room temperature
2. filtrationfiltered
3. dissolutionThe resulting solid was dissolved in 2N sodium hydroxide (350 ml)
4. extractionextracted with diethyl ether (2×300 ml)
5. customThe aqueous layer was separated
6. filtrationThe resulting precipitate was filtered
7. washwashed with water

ORD record

ord-906488ecad034fc4ba13b69fa4693560

Source dataset

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05563141