Diethyl Ether → 1-(2-Bromopyridin-4-yl)-propan-1-ol

To a chilled (−78° C.) solution of 2-bromo-pyridine-4-carbaldehyde (7.0 g, 38 mmol) in THF (200 mL) was added a 2 M solution of ethylmagnesium chloride in ether (23.5 mL, 47.0 mmol) over a 10 minute period. After 15 minutes, the mixture was gradually warmed to room temperature over 1 hour. The reaction was quenched by the slow addition of saturated aqueous NH4Cl (100 mL) and extracted with EtOAc (2×200 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated to afford a brown oil. The crude material was purified by silica gel chromatography eluting with a gradient of 20-40% EtOAc in hexanes to afford 1-(2-bromo-pyridin-4-yl)-propan-1-ol.

1. customThe reaction was quenched by the slow addition of saturated aqueous NH4Cl (100 mL)
2. extractionextracted with EtOAc (2×200 mL)
3. washThe combined organic layers were washed with brine
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. customto afford a brown oil
7. customThe crude material was purified by silica gel chromatography
8. washeluting with a gradient of 20-40% EtOAc in hexanes

ORD record

ord-e4b68cb6afd34f0b88cb623d7067845f

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063065B2