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

HRID 712662Notes

Reaction equation

HRID 712662 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.Br[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:10]([O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 153891983-(Benzyloxy)-5-bromopyridineYield 34.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 5-bromo-pyridin-3-ol (1.9 g, 10.9 mmol) in acetonitrile (152 mL) is added bromomethyl-benzene (2.1 g, 12.0 mmol) and potassium carbonate (4.5 g, 32.8 mmol). The resultant mixture is stirred at room temperature for 16 h. The crude product is purified by silica gel column to afford 3-benzyloxy-5-bromo-pyridine (1.0 g).

Workup

  1. customThe crude product is purified by silica gel column

Sources & evidence

ORD record
ord-b7910708363c46bd82aa60c94a64f8b7
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

Loading…