Bromomethyl 4-methoxyphenyl ketone → HCID 887806, compound

HRID 1948679Notes

Reaction equation

HRID 1948679 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[O:18]>C(#N)C>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[O:18])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 887806HCID 887806, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

24 g of potassium carbonate are added to a solution of 20 g (0.115 mol) of 4-bromophenol and 26.5 g (0.115 mol) of 2-bromo-4′-methoxyacetophenone in 400 of acetonitrile, and the reaction mixture is heated under reflux for five hours. The precipitate is subsequently filtered off, the filtrate is evaporated to dryness, the residue is taken up in 10 ml of water, and the aqueous solution is extracted twice with 10 ml of ethyl acetate each time. The combined organic phases are washed with 10 ml of saturated sodium chloride solution and dried over sodium sulfate. After the solvent has been stripped off, the residue is triturated with 50 ml of diethyl ether, and the resultant crystalline product is filtered off with suction in vacuo, giving 35.5 g of 2-(4-bromophenoxy)-1-(4-methoxyphenyl)ethanone as beige solid.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for five hours
  3. filtrationThe precipitate is subsequently filtered off
  4. customthe filtrate is evaporated to dryness
  5. extractionthe aqueous solution is extracted twice with 10 ml of ethyl acetate each time
  6. washThe combined organic phases are washed with 10 ml of saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. customthe residue is triturated with 50 ml of diethyl ether
  9. filtrationthe resultant crystalline product is filtered off with suction in vacuo

Sources & evidence

ORD record
ord-0943355fad0e42cf85017c39819d9a0a
Source dataset
uspto-grants-2013_03
Patent number
US08399509B2

Reaction notes

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