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

Temperature

0 °C

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

ORD record

ord-82b3b230c7b64b8f9934624f5b84e1f2

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09340503B2