Phenacyl bromide → 2-(2-Bromophenoxy)-1-phenylethan-1-one

HRID 1761916Notes

Reaction equation

HRID 1761916 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[CH2:11](Br)[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13]>O1CCCC1>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C:12](=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 72442-BromophenolHCID 24758Sodium hydride

Product 1

HCID 30163542-(2-Bromophenoxy)-1-phenylethan-1-oneYield 52.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

(1)-(i) A suspension of 6.72 g of 60% sodium hydride in 40 ml of tetrahydrofuran is added dropwise to a solution of 24.17 g of 2-bromophenol in 210 ml of tetrahydrofuran at 4° C. and the mixture is stirred at the same temperature for 15 minutes. A solution of 30.66 g of phenacyl bromide in 60 ml of tetrahydrofuran is added dropwise to the mixture. The mixture is stirred at the same temperature for 30 minutes and further refluxed for 2.5 hours. The reaction mixture is evaporated to remove solvent, and water is added to the residue. The aqueous mixture is extracted with ethyl acetate and the extract is washed, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography and recrystallized from a mixture of ethyl acetate and n-hexane to give 21.49 g of (2-bromophenyl)(benzoylmethyl)ether as colorless needles.

Workup

  1. stirringThe mixture is stirred at the same temperature for 30 minutes
  2. temperaturefurther refluxed for 2.5 hours
  3. customThe reaction mixture is evaporated
  4. customto remove solvent, and water
  5. additionis added to the residue
  6. extractionThe aqueous mixture is extracted with ethyl acetate
  7. washthe extract is washed
  8. customdried
  9. customevaporated
  10. customto remove solvent
  11. customThe residue is purified by silica gel column chromatography
  12. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-59a958539e2348f290a571357b0a7000
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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