Water → HCID 9212449, compound

HRID 2197896Notes

Reaction equation

HRID 2197896 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][C:13]([C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)=[O:14].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([O:21][C:18]2[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH3:12])=[CH:16][CH:17]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 27949042-Bromo-5-chloronitrobenzene

Product 1

HCID 9212449HCID 9212449, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-Bromo-4-chloro-2-nitrobenzene (5 g, 21.2 mmol) was added to a solution of 4-hydroxyacetophenone (2.87 g, 21.1 mmol), and K2CO3 (7.28 g, 0.052 mol) in DMF (50 mL). The mixture was heated at 80° C. for 15 h. The reaction was poured into water. The aqueous phase was extracted with ethyl acetate (2×) and the combined phases were washed with water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the crude title compound. The crude product was purified by flash chromatography eluting with (hexanes/ethyl acetate 70:30) to give the title compound (4.8 g, 77.8%).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  2. washthe combined phases were washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customgiving the crude title compound
  7. customThe crude product was purified by flash chromatography
  8. washeluting with (hexanes/ethyl acetate 70:30)

Sources & evidence

ORD record
ord-74fd80d3a21047c6b8379c83de2f5c18
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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