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

HRID 340220Notes

Reaction equation

HRID 340220 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Ag+2]>[CH2:9]([O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 153891983-(Benzyloxy)-5-bromopyridine

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 5-bromopyridin-3-ol (1.0 eq.), benzyl bromide (1.2 eq.), and silver carbonate (1.3 eq.) in toluene (0.1 M) was heated to 50° C. and stirred for 18 hours. After cooling to room temperature, the reaction mixture was filtered, eluting with ethyl acetate. The filtrate was concentrated en vacuo into a residue that was purified by a COMBIFLASH® system (ISCO) using 20% ethyl acetate in hexane to give 3-(benzyloxy)-5-bromopyridine.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washeluting with ethyl acetate
  3. concentrationThe filtrate was concentrated en vacuo into a residue that
  4. customwas purified by a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-89c23888c9af480984d3a237806e088c
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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