Ethyl bromoacetate → HCID 20375653, compound

HRID 1448795Notes

Reaction equation

HRID 1448795 reaction equation
[O:1]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(#N)C>[Br-:14].[CH2:19]([O:18][C:16](=[O:17])[CH2:15][N+:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)[CH3:20]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 2005103-Phenoxypyridine

Product 1

HCID 20375653HCID 20375653, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 17.1 g of 3-phenoxypyridine [J. Amer. Chem. Soc 59, 297 (1937)] in 100 ml of acetonitrile is added 16.7 g of ethyl bromoacetate and the solution is refluxed for 8 hours. The resulting mixture is concentrated at reduced pressure and the crystalline solid is isolated by filtration to yield 1-(2-ethoxy-2-oxoethyl)-3-phenoxypyridinium bromide; mp 125°-126° C. after recrystallization from acetonitrile-diethyl ether.

Workup

  1. temperaturethe solution is refluxed for 8 hours
  2. concentrationThe resulting mixture is concentrated at reduced pressure
  3. customthe crystalline solid is isolated by filtration

Sources & evidence

ORD record
ord-29ebd4fa5934430da8258585cd8ffab2
Source dataset
uspto-grants-1980_02
Patent number
US04187311

Reaction notes

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