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

Temperature

54 °C

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

1. customranging from 40° C. to 58° C.
2. stirringwhich was stirred for another 30 minutes at 65° C
3. temperatureThe reaction solution was cooled to room temperature
4. customwhich was separated
5. extractionThe aqueous layer was further extracted with ethyl acetate twice
6. washwashed with water three times and saline once
7. dry with materialwas then dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under a reduced pressure
10. additionDiethyl ether was added to the residue
11. concentrationthis was concentrated under a reduced pressure

ORD record

ord-b33c350fc2674194851a844c71265e14

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513287B2