Ethyl Acetate → HCID 23042157, compound

HRID 2166101Notes

Reaction equation

HRID 2166101 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11](O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](=[O:18])([O-])[O-].[K+].[K+].[Br:21][C:22]1[S:23][CH:24]=[C:25](CCl)[CH:26]=1.C(OCC)(=O)C>CN(C)C=O>[Br:21][C:22]1[S:23][CH:24]=[C:25]([CH2:15][O:18][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[O:1][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:26]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 132544-PhenoxyphenolHCID 128741092-Bromo-4-(chloromethyl)thiophene

Product 1

HCID 23042157HCID 23042157, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

7.44 g of 4-phenoxyphenol and 5.52 g of potassium carbonate are stirred in 50 ml of anhydrous dimethylformamide for 1 hour at 70° C. 5.52 g of 2-bromo-4-chloromethylthiophene is then dripped in, and the mixture is stirred for a further 12 hours at 80° C., and at room temperature (approx. 20° C.) overnight. The mixture is then stirred into 500 ml of ethyl acetate and washed three times with water. After drying over sodium sulfate and removal of the solvent, the residue is recrystallized from n-hexane. There is obtained 10.7 g of 2-bromo-4-[(phenoxyphenoxy)-methyl]-thiophene; colorless powder; m.p.: 90° C.

Workup

  1. customat room temperature
  2. custom(approx. 20° C.) overnight
  3. washwashed three times with water
  4. dry with materialAfter drying over sodium sulfate and removal of the solvent
  5. customthe residue is recrystallized from n-hexane

Sources & evidence

ORD record
ord-ec1b8f9b6ccb498997b34037395a1d9a
Source dataset
uspto-grants-1990_07
Patent number
US04943584

Reaction notes

Loading…