Potassium Carbonate → Ethyl 2-(3-bromophenoxy)-2-methylpropanoate

HRID 2234861Notes

Reaction equation

HRID 2234861 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 5197437Ethyl 2-(3-bromophenoxy)-2-methylpropanoateYield 89%

Procedure

25 g (144.5 mmol) of 3-bromophenol are placed in the presence of K2CO3 (21 g, 152 mmol) in 75 ml of ethyl 2-bromoisobutyrate and heated to reflux for 7 h. After elimination of K2CO3 by filtration, the reaction medium is dry concentrated. After purification by flash chromatography on silica (petroleum ether:AcOEt 90:10), 37 g of intermediate 10d are collected in the form of clear oil (yield=89%). TLC silica gel 60 F 254 Merck, petroleum ether:AcOEt 90:10, Rf=0.40.

Workup

  1. temperatureheated
  2. temperatureto reflux for 7 h
  3. filtrationAfter elimination of K2CO3 by filtration
  4. customthe reaction medium is dry
  5. concentrationconcentrated
  6. customAfter purification by flash chromatography on silica (petroleum ether:AcOEt 90:10), 37 g of intermediate 10d

Sources & evidence

ORD record
ord-6fd7990a9eae452685efcf28467d9482
Source dataset
uspto-grants-2010_05
Patent number
US07713971B2

Reaction notes

Loading…