Sodium Chloride → 2-Bromo-1-(2,4-difluorophenoxy)-4-nitrobenzene

HRID 930858Notes

Reaction equation

HRID 930858 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[OH:20].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[Na+]>CS(C)=O.O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:20][C:14]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=1[F:12]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 696992-Bromo-1-fluoro-4-nitrobenzeneHCID 1230512,4-Difluorophenol

Product 1

HCID 867049232-Bromo-1-(2,4-difluorophenoxy)-4-nitrobenzeneYield 100.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-bromo-1-fluoro-4-nitrobenzene (15 g, 68 mmol), 2,4-difluorophenol (7.82 ml, 82 mmol), and cesium carbonate (26.7 g, 82 mmol) in dimethylsulfoxide (75 mL) was heated to 110° C. for 1 hour. The reaction mixture was cooled to ambient temperature and water (1000 mL) and saturated aqueous sodium chloride (1000 mL) were added. The mixture was extracted with ethyl acetate (3×200 mL). The combined organics were washed with saturated aqueous sodium chloride, dried (anhydrous magnesium sulfate), filtered, and concentrated under reduced pressure to provide the title compound (22.5 g, quantitative).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
  3. washThe combined organics were washed with saturated aqueous sodium chloride
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79fd50099c3143bd8a393ca065c1eeaf
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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