Acetaldehyde → HCID 75480808, compound

Temperature

-78 °C

To a 1000 mL 3-neck flask was added 2-bromo-5-fluoropyridine (8.80 g, 50 mmol) and THF (200 mL) at −78° C. followed by dropwise addition of LDA (20.0 mL, 50 mmol, 2.5 M). After stirring at −78° C. for 4 h, acetaldehyde (3.1 mL, 55 mmol) was added dropwise via syringe. The contents were removed from the cold bath and stirred at room temperature overnight. The mixture was diluted with H2O (150 mL), and vigorously stirred for 5 min. The contents were extracted with ethyl ether (3×150 mL), the combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to afford a yellow oil. The crude product was passed through a short silica column (eluent: 3:1 PE/EtOAc) to afford 1-(2-bromo-5-fluoropyridin-4-yl)ethanol as a white solid (9.5 g, 86%). ESI MS m/z=220 (M+1)

1. customThe contents were removed from the cold bath
2. stirringstirred at room temperature overnight
3. additionThe mixture was diluted with H2O (150 mL)
4. stirringvigorously stirred for 5 min
5. extractionThe contents were extracted with ethyl ether (3×150 mL)
6. dry with materialthe combined organic layers were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto afford a yellow oil

ORD record

ord-771a628f29d648e582f4b74749afc77b

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260425B2