Water → 2-((4-Bromobenzyl)oxy)pyridine

Temperature

54 °C

To a solution of 4-bromobenzyl alcohol (25 g, 130 mmol) in N,N-dimethyl formamide (125 mL) was added potassium tert-butoxide (15.8 g, 141 mmol) at room temperature, which was stirred at 54° C. for 10 minutes. To this reaction solution was added 2-fluoropyridine (15 mL, 154 mmol) at from 40° C. to 58° C., which was further stirred for 30 minutes at 65° C. The reaction solution was allowed to room temperature, water and ethyl acetate were added, and liquid separation was carried out. The aqueous layer was further extracted with ethyl acetate (twice). The ethyl acetate layers were combined, washed with water (3 times) and sodium chloride water (once), dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure. Diethyl ether was added to the residue, which was concentrated under a reduced pressure to obtain the title compound (34 g) as a crude product.

1. stirringwas further stirred for 30 minutes at 65° C
2. customwas allowed to room temperature
3. customliquid separation
4. extractionThe aqueous layer was further extracted with ethyl acetate (twice)
5. washwashed with water (3 times) and sodium chloride water (once),
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under a reduced pressure
9. additionDiethyl ether was added to the residue, which
10. concentrationwas concentrated under a reduced pressure

ORD record

ord-b21ecb7395634b9d883ae8a1a2c2f206

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2