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

HRID 1425596Notes

Reaction equation

HRID 1425596 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[N:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:16][C:13]1[CH:12]=[CH:11][C:10]([Br:9])=[N:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 160946965-(Benzyloxy)-2-bromopyridineYield 82.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzyl bromide (1.367 ml, 11.49 mmol) was added to a solution containing 6-bromopyridin-3-ol (2 g, 11.49 mmol) and Potassium carbonate (2.383 g, 17.24 mmol) in Acetone (Volume: 38.3 ml). Let the reaction stir for 4 hours. Concentrated and purified by Combiflash using 15% ethyl acetate in hexanes to afford 5-(benzyloxy)-2-bromopyridine (2.5 g, 9.47 mmol, 82% yield).

Workup

  1. concentrationConcentrated
  2. custompurified by Combiflash

Sources & evidence

ORD record
ord-c7442dcbaf634299aa76133cbe14ff24
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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