Benzyl Bromide → 2-Benzyloxy-5-bromopyridine

HRID 919212Notes

Reaction equation

HRID 919212 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[CH2:10]([O:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 5995285-Bromo-2-hydroxypyridine

Product 1

HCID 111081912-Benzyloxy-5-bromopyridineYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromopyridin-2(1H)-one (1.28 g, 7.36 mmol) and Ag2CO3 (3 g, 11.04 mmol) in toluene (50 mL) was added (bromomethyl)benzene (1.25 g, 7.36 mmol) dropwise and the reaction mixture was stirred at 100° C. over night. The reaction mixture was filtered through a short pad of silica gel and washed with DCM. The filtrate was concentrated to yield the title compound as light yellow oil (1.8 g, 95%).

Workup

  1. filtrationThe reaction mixture was filtered through a short pad of silica gel
  2. washwashed with DCM
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4ff009f90e07460f87806310babc8d06
Source dataset
uspto-grants-2016_03
Patent number
US09273026B2

Reaction notes

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