Ethyl Acetate → HCID 23090823, compound

HRID 1820004Notes

Reaction equation

HRID 1820004 reaction equation
Br[CH:2]([CH3:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)=[O:4].[OH:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([CH3:24])=[O:23])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH:2]([O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][C:22](=[O:23])[CH3:24])=[CH:19][CH:20]=2)[CH3:13])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 532260HCID 532260, compoundHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 23090823HCID 23090823, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-N-(4-bromophenyl)propanamide (3.00 g, 10.2 mmol), 1-(4-hydroxyphenyl)acetone (1.54 g, 10.2 mmol) and potassium carbonate (2.83 g, 20.5 mmol) in DMF (20 ml) was stirred at room temperature for 4 hrs. Ethyl acetate was added to the reaction mixture, and the mixture was washed with 1N aqueous sodium hydroxide solution and brine. The solvent was evaporated under reduced pressure, and the obtained crude crystals were recrystallized from isopropyl ether-ethyl acetate to give the title compound (2.75 g).

Workup

  1. washthe mixture was washed with 1N aqueous sodium hydroxide solution and brine
  2. customThe solvent was evaporated under reduced pressure
  3. customthe obtained crude crystals
  4. customwere recrystallized from isopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-0d17a598d52d4807b1c82fcb19543e1e
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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