Dimethylformamide → 5-(Benzyloxy)-2-chloropyridine

HRID 1806089Notes

Reaction equation

HRID 1806089 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:10]([O:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][CH:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 100137175-(Benzyloxy)-2-chloropyridineYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Chloropyridin-3-ol (30.00 g, 231.6 mmol), 1-(bromomethyl)benzene (43.57 g, 254.7 mmol), and potassium carbonate (80.01 g, 579.0 mmol) were added to DMF (500 mL) and stirred at ambient temperature overnight. Water was added and extracted with ether. The organic phase was washed with 1M NaOH, dried, filtered, and concentrated to provide the title compound (50.8 g, 99.86% yield).

Workup

  1. extractionextracted with ether
  2. washThe organic phase was washed with 1M NaOH
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b8840c68926e473688014f1c47135503
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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