Benzyl Bromide → 2-Benzyloxy-5-bromopyridine

HRID 574175Notes

Reaction equation

HRID 574175 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-9665073dbe354264a876e074aa0deb34
Source dataset
uspto-grants-2015_05
Patent number
US09034874B2

Reaction notes

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