Potassium Carbonate → 2-Chloro-3-(2-phenoxyethoxy)pyridine

HRID 493337Notes

Reaction equation

HRID 493337 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:7]([O:8][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 811362-Chloro-3-pyridinol

Product 1

HCID 235095692-Chloro-3-(2-phenoxyethoxy)pyridineYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-3-hydroxypyridine (3.0 g, 23.1 mmol), β-bromophenetole (4.66 g, 23.2 mmol), and K2CO3 (8.0 g, 57.9 mmol) in DMF (50 mL) was heated at 100° C. for 1.5 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and H2O. The organic phase was dried (MgSO4), filtered, and the solvent evaporated. The solid residue was triturated with a small amount of ether and dried (65° C., 1 mmHg) to afford 4.23 g (74%) of the title product as white crystals: mp 77-78° C. Anal. (C13H12ClNO2) C, H, N.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and H2O
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe solid residue was triturated with a small amount of ether
  7. customdried (65° C., 1 mmHg)

Sources & evidence

ORD record
ord-5edfd5a87093474a9272acd293fc49b1
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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