Water → 4-Methylpyridine-3-Boronic Acid

A solution of 3-bromo-4-methylpyridine (5.96 g) in ether (20 ml) was added dropwise to n-butyl lithium in hexane (1.57M;22 ml) in ether (100 ml) at -78° under nitrogen. After 10 min stirring at -78° triisopropylborate (10.2 ml) was added during 2 min. The mixture was stirred at -78° for 30min and allowed to warm to room temperature during 2 h. Water (30 ml) was added and the organic layer was extracted with aqueous sodium hydroxide (0.5N; 33 ml). The combined aqueous layers were washed with ether (30 ml) and then acidified to pH6 with hydrochloric acid (2N). The mixture was stirred until the resulting gum had solidified. Filtration gave the title compound as a white solid (1.5 g).

1. additionwas added during 2 min
2. extractionthe organic layer was extracted with aqueous sodium hydroxide (0.5N; 33 ml)
3. washThe combined aqueous layers were washed with ether (30 ml)
4. stirringThe mixture was stirred until the resulting gum
5. filtrationFiltration

ORD record

ord-9b7cc6118cdc4053ab4ac38abe82affc

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05358948