Phenol → HCID 86704948, compound

HRID 2170220Notes

Reaction equation

HRID 2170220 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 696992-Bromo-1-fluoro-4-nitrobenzene

Product 1

HCID 86704948HCID 86704948, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

2-Bromo-1-fluoro-4-nitrobenzene (2.5 g, 11.4 mmol), phenol (1.28 g, 13.6 mmol), and cesium carbonate (4.44 g, 13.6 mmol) were combined in dimethyl sulfoxide (140 mL) and heated at 110° C. for 1 hour. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride. The combined organics were washed with saturated aqueous sodium chloride, dried (anhydrous magnesium sulfate), filtered, and concentrated to afford the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride
  2. washThe combined organics were washed with saturated aqueous sodium chloride
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c784d00f3a7e4b46bb4f8630868024e1
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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