Phenacyl bromide → HCID 8176949, compound

HRID 1167614Notes

Reaction equation

HRID 1167614 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:14][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 15285Phenol, 4-methoxy-2-nitro-

Product 1

HCID 8176949HCID 8176949, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under an inert atmosphere, 4-methoxy-2-nitrophenol (1.5 g; 8.86 mmol) is dissolved in 30 ml of acetone, and then 2-bromoacetophenone (1.5 eq.; 13.29 mmol; 2.79 g) and also potassium carbonate (1.2 eq.; 10.64 mmol; 1.47 g) are added. The mixture is stirred vigorously, at reflux, for 3 hours. After returning to ambient temperature, the potassium carbonate is filtered off, the filtrate is evaporated and the residue is taken up in a water/ethyl acetate mixture. The organic phase is dried over MgSO4 and then concentrated under reduced pressure. The crude reaction product is purified by flash chromatography on silica gel (eluant: PE/AcOEt (8/2)). The title product is obtained in the form of a yellow solid.

Workup

  1. temperatureat reflux, for 3 hours
  2. customAfter returning to ambient temperature
  3. filtrationthe potassium carbonate is filtered off
  4. customthe filtrate is evaporated
  5. dry with materialThe organic phase is dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude reaction product
  8. customis purified by flash chromatography on silica gel (eluant: PE/AcOEt (8/2))

Sources & evidence

ORD record
ord-66858e6a64cc4e5ba32a2e458d3d1ab8
Source dataset
uspto-grants-2003_09
Patent number
US06620809B2

Reaction notes

Loading…