Water → 2-Bromonicotinaldehyde

To a stirring solution of 2-bromopyridine (5.13 g, 3.2 mmol) in THF (90 ml) at −78° C. was slowly added lithium diisopropylamide (LDA) (2 M in THF, 17.9 ml, 3.6 mmol) and the resulting reaction mixture allowed to stir for three hours. To the reaction mixture was then slowly added DMF (9.49 g, 130 mmol) in THF (10 ml). The reaction mixture was stirred at −78° C. for 30 min, and was then allowed to warm to room temperature. Water (100 mol) was added and then the reaction mixture was extracted with ethyl acetate three times. The combined organic layers were dried over MgSO4. The solvent was removed and the resulting residue purified over silica gel chromatography eluted with hexane, to yield 2-bromo-pyridine-3-carbaldehyde as a white solid.

1. customat −78° C.
2. customthe resulting reaction mixture
3. stirringThe reaction mixture was stirred at −78° C. for 30 min
4. extractionthe reaction mixture was extracted with ethyl acetate three times
5. dry with materialThe combined organic layers were dried over MgSO4
6. customThe solvent was removed
7. customthe resulting residue purified over silica gel chromatography
8. washeluted with hexane

ORD record

ord-04c7f331b8a04e93b697f8e665ad2fc8

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07053101B2