Ethyl bromoacetate → Ethyl [5-acetyl-2-(2,6-difluorobenzyloxy)-phenoxy]-acetate

HRID 1596704Notes

Reaction equation

HRID 1596704 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:18](=[O:20])[CH3:19])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[F:17].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:18]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[C:11]([F:17])=[CH:12][CH:13]=[CH:14][C:15]=2[F:16])=[C:2]([CH:3]=1)[O:1][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 105167073'-Hydroxy-4'-(2,6-difluorobenzyloxy)-acetophenone

Product 1

HCID 15907792Ethyl [5-acetyl-2-(2,6-difluorobenzyloxy)-phenoxy]-acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3′-hydroxy-4′-(2,6-difluorobenzyloxy)-acetophenone (15.0 g, 53.96 mmol), ethyl bromoacetate (7.2 mL, 64.75 mmo), and K2CO3 (14.9 g, 107.92 mmol) in acetone (350 mL) is refluxed 18 hours. After cooling, the mixture is filtered, and the filtrate is concentrated in vacuo. Recrystallizaton from EtOAc yields ethyl [5-acetyl-2-(2,6-difluorobenzyloxy)-phenoxy]-acetate.

Workup

  1. temperatureis refluxed 18 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-8111e3f7e3af458fb897d9d6e8795a1a
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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