Phenol → 4-Bromo-2-nitro-1-phenoxybenzene

HRID 449109Notes

Reaction equation

HRID 449109 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 161094494-Bromo-2-nitro-1-phenoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-2-fluoronitrobenzene (1.10 g, 5.0 mmol), phenol (0.52 g, 5.5 mmol) and K2CO3 powder (0.83 g, 5.0 mmol) in DMF (10 mL) was stirred at 80° C. for 3 h. The mixture was concentrated under reduced pressure, and the residue was partitioned between AcOEt and water. The separated organic layer was washed with 1M aqueous HCl and saturated NaCl solution. After the organic layer was dried over Na2SO4, the solvent was removed to give desired product which was used for next step without further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between AcOEt and water
  3. washThe separated organic layer was washed with 1M aqueous HCl and saturated NaCl solution
  4. dry with materialAfter the organic layer was dried over Na2SO4
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-08ff33345c49439892e58344b66489e5
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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