Water → HCID 68461162, compound

HRID 2197911Notes

Reaction equation

HRID 2197911 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][CH:18]=[C:19]([OH:21])[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:19]2[CH:20]=[C:15]([C:13](=[O:14])[CH3:12])[CH:16]=[CH:17][CH:18]=2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 84873-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 27949042-Bromo-5-chloronitrobenzene

Product 1

HCID 68461162HCID 68461162, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-Bromo-4-chloro-2-nitrobenzene (10 g, 42.2 mmol) was added to a solution of 3-hydroxyacetophenone (5.5 g, 42.2 mmol), and K2CO3 (11.7 g, 84.6 mmol) in DMF (50 mL). The mixture was heated at 80° C. for 16 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 title compound. The crude product was purified by flash chromatography eluting with (hexanes/ethyl acetate 70:30) to give the title compound (8.6 g, 70%).

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

Sources & evidence

ORD record
ord-85770af201ad422584e1ff5f75d97fcb
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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