Benzyl Bromide → 5-(Benzyloxy)-2-bromopyridine

2-Bromo-5-hydroxypyridine (347 mg, 2 mmol) in DMF (3 mL) was added dropwise over a period of 10 min to a suspension of NaH (88 mg, 2.3 mmol) in DMF (2 mL) at 0° C. under Ar(g). The reaction mixture was then stirred at rt for 10 min, after which it was again cooled down at 0° C., and benzyl bromide (0.25 mL, 2.1 mmol) was added. The reaction mixture was stirred at rt for 2.5 h, after which it was poured onto brine (20 mL) and EtOAc (20 mL) was added. The phases were separated and the aqueous phase was extracted with EtOAc (20 mL). The organic phases were combined, dried over MgSO4, filtered and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with hexane/EtOAc (95:5 to 90:10) to furnish I as a colourless oil (380 mg, 72%).

1. temperatureafter which it was again cooled down at 0° C.
2. stirringThe reaction mixture was stirred at rt for 2.5 h
3. additionwas added
4. customThe phases were separated
5. extractionthe aqueous phase was extracted with EtOAc (20 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customsubsequently evaporated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography
10. washeluting with hexane/EtOAc (95:5 to 90:10)

ORD-Eintrag

ord-a5c72394a02a403c9619268dfe3b6390

Quelldatensatz

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08748458B2