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

HRID 632735Notes

Reaction equation

HRID 632735 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 at 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 2-bromo-1-(2,4-difluorophenoxy)-4-nitrobenzene (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-9c461f1294754ebabb4b7f6a40990527
Source dataset
uspto-grants-2016_04
Patent number
US09321765B2

Reaction notes

Loading…