Dimethylformamide → 5-(Benzyloxy)-2-chloropyridine

HRID 335162

Reaction equation

HRID 335162 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-cf8d630a2c4040d8bce771347a161879
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Linked notes

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