Benzyl Alcohol → 3-(Benzyloxy)-5-bromopyridine

Temperature

70 °C

Under a nitrogen atmosphere, small pieces of sodium (1.48 g, 64.4 mmol) were added to benzyl alcohol (17.11 g, 158 mmol), and the mixture was stirred and heated at 70° C. for 18 h. To the stirring, viscous mixture was added 3,5-dibromopyridine (5.00 g, 21.1 mmol), copper powder (0.255 g, 4.0 mmol) and benzyl alcohol (15 mL). The mixture was further heated at 100° C. for 48 h. The reaction mixture was allowed to cool to ambient temperature, diluted with water (50 mL), and extracted with ethyl ether (5×50 mL). The combined ether layers were dried (Na2SO4), filtered, and concentrated. Distillation at 68-72° C. and 2.6 mm Hg removed excess benzyl alcohol. The remaining yellowish, brown residue was purified by vacuum distillation at 0.05 mm Hg to yield 3.17 g (38.0%) of a white, crystalline solid, mp 64-66° C.

1. temperatureThe mixture was further heated at 100° C. for 48 h
2. temperatureto cool to ambient temperature
3. extractionextracted with ethyl ether (5×50 mL)
4. dry with materialThe combined ether layers were dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. distillationDistillation at 68-72° C.
8. custom2.6 mm Hg removed excess benzyl alcohol
9. distillationThe remaining yellowish, brown residue was purified by vacuum distillation at 0.05 mm Hg
10. customto yield 3.17 g (38.0%) of a white, crystalline solid, mp 64-66° C.

ORD record

ord-18eb24d6d5c04d9c970605366319efcf

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627648B1