Water → 1-[3-Bromo-4-(phenylmethoxy)phenyl]-2-propanone

HRID 1375987Notes

Reaction equation

HRID 1375987 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH2:23][C:24]([CH3:26])=[O:25])[CH:19]=[CH:20][C:21]=1[OH:22].O>CN(C=O)C>[CH2:7]([O:22][C:21]1[CH:20]=[CH:19][C:18]([CH2:23][C:24]([CH3:26])=[O:25])=[CH:17][C:16]=1[Br:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 247210551-(3-Bromo-4-hydroxyphenyl)propan-2-one

Product 1

HCID 230805631-[3-Bromo-4-(phenylmethoxy)phenyl]-2-propanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.7 g) and benzyl bromide (2.3 ml) were added to a solution of 1-(3-bromo-4-hydroxyphenyl) acetone (4.0 g) in DMF (40 ml) and the mixture was stirred at room temperature for six hours. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate-n-hexane) to obtain 1-[4-(benzyloxy)-3-bromophenyl]acetone (3.65 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-03c5e4a9e73a43d2a91aa0627c528459
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

Loading…