Benzyl Chloride → 2-(Benzyloxy)-6-chloropyridine

HRID 1471240

Reaction equation

HRID 1471240 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([O:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 1785160256-chloropyridin-2-ol

Product 1

HCID 112644642-(Benzyloxy)-6-chloropyridineYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 5.0 g 6-chloro-2-hydroxypyridine, 5.3 g potassium carbonate and 75 ml N,N-dimethylformamide. After cooling to 5 C under nitrogen, 5.9 g of benzyl chloride were added drop wise and the reaction mixture was warmed to 60 C for 3 hours. After cooling to 10 C, the reaction mixture was quenched with 75 ml of water and the product was extracted with ethyl acetate and washed with water. Following solvent removal, the product was purified by silica gel chromatography using 5% ethyl acetate in hexane to give a clear colorless oil 7.9 g.

Workup

  1. temperatureAfter cooling to 5 C under nitrogen
  2. temperaturethe reaction mixture was warmed to 60 C for 3 hours
  3. temperatureAfter cooling to 10 C
  4. customthe reaction mixture was quenched with 75 ml of water
  5. extractionthe product was extracted with ethyl acetate
  6. washwashed with water
  7. customFollowing solvent removal
  8. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f03e2f09d3db47349b11affb9d07dde9
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Linked notes

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