Hydrochloric Acid → 3-(Pyridin-2-yl)benzaldehyde

Temperature

-78 °C

EX-587A) To a THF solution (8 mL) of 2-bromopyridine (1.30 g, 8.23 mmol) at −78° C. was added 1.6 M n-BuLi in hexanes (5.3 mL, 8.48 mmol). The resulting dark red solution was stirred at −78° C. for 10 min, and a solution of 0.5 M ZnCl2 in THF (18 mL, 9.0 mmol) was added giving a light brown slurry. After warming to room temperature, 3-bromobenzaldehyde (0.816 mL, 7.0 mmol) and Pd(PPh3)4 (0.242 g, 0.21 mmol) were added, and the mixture was stirred for 18 h at room temperature under argon. The reaction mixture was poured into 1 N HCl (30 mL) and washed with diethyl ether. The aqueous layer was neutralized with NaHCO3 and extracted with diethyl ether. The solvent was removed in vacuo to give the crude product as an oil. Purification by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane gave 0.49 g (38%) of the desired 3-(2-pyridinyl)benzaldehyde product as a colorless oil.

1. customgiving a light brown slurry
2. temperatureAfter warming to room temperature
3. stirringthe mixture was stirred for 18 h at room temperature under argon
4. washwashed with diethyl ether
5. extractionextracted with diethyl ether
6. customThe solvent was removed in vacuo
7. customto give the crude product as an oil
8. customPurification by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane

ORD record

ord-e47b45b1efe2452bb90f8181f965c6c8

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06586433B2