Water → 1-(2,4-Dichlorophenoxy)-3-fluoro-2-nitrobenzene

HRID 746739Notes

Reaction equation

HRID 746739 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[Cs+].[Cs+].[F:16][C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([F:16])[C:18]=1[N+:24]([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 84492,4-DichlorophenolHCID 10796Cesium carbonateHCID 677672,5-Difluoronitrobenzene

Product 1

HCID 551009431-(2,4-Dichlorophenoxy)-3-fluoro-2-nitrobenzeneYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Under a nitrogen atmosphere, 2,4-dichlorophenol (500 mg, 3.067 mmol) was diluted in DMF (15 mL). Cesium carbonate (3 g, 9.202 mmol) was then added followed by 2,5-difluoronitro-benzene (976 mg, 6.135 mmol). The reaction was heated to 90° C. and allowed to stir for 12 hours. Then, 500 uL of water was added and was heated for an additional 4 hours. The reaction was then quenched with water (30 mL) and extracted with ethyl acetate (3×60 mL). The organic extracts were dried over sodium sulfate and concentrated. Silica gel chromatography (5%-20% EtOAc/hexanes) gave 1-(2,4-dichlorophenoxy)-3-fluoro-2-nitrobenzene (257 mg, 30%).

Workup

  1. temperaturewas heated for an additional 4 hours
  2. customThe reaction was then quenched with water (30 mL)
  3. extractionextracted with ethyl acetate (3×60 mL)
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c03e0f3b55c44bc7b06a9aa8c42ff756
Source dataset
uspto-grants-2008_07
Patent number
US07393873B2

Reaction notes

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