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

Temperature

54 °C

To a solution of 4-bromobenzyl alcohol (25 g, 130 mmol) in N,N-dimethylformamide (125 mL) was added potassium tert-butoxid 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 of 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 to separate the reaction solution. The aqueous layer was further extracted (twice) with ethyl acetate. This was combined with an ethyl acetate layer, washed with water (three times) and saline (once), and was 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 titled compound (34 g).

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

ORD record

ord-ec9be5a30e994da99f383400a3633ded

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188119B2