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

Temperature

54 °C

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

1. additionwas added at a temperature from 40° C. to 58° C.
2. stirringwhich was stirred at 65° C. for 30 minutes
3. temperatureThe reaction solution was cooled to room temperature
4. custompartitioned into water and ethyl acetate
5. extractionThe water layer was further extracted with ethyl acetate (twice)
6. washwashed with water (3 times) and aqueous sodium chloride (once),
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under a reduced pressure
10. additionTo the residue was added diethyl ether, which
11. concentrationwas then concentrated under a reduced pressure

ORD record

ord-d481f39b0ae74575b33f79fe0910fe5f

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507530B2