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

HRID 2358676Notes

Reaction equation

HRID 2358676 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[Br:14][C:15]1[CH:20]=[CH:19][C:18](F)=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=1>CN(C=O)C.CCOC(C)=O>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:17]([N+:22]([O-:24])=[O:23])[CH:16]=1

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of phenol (2.35 g, 25.0 mmol) and K2CO3 (9.4 g, 68.1 mmol) in 40 mL of DMF was heated at 100° C. with 4-bromo-1-fluoro-2-nitrobenzene (5.0 g, 22.7 mmol) with stirring for 24 hours. Cooled to room temperature and diluted with EtOAc. Washed with water and dried the organic layer over MgSO4. Filtered and concentrated under vacuum giving the title compound, which was purified by silica gel column chromatography eluting with 15% EtOAc/hexane giving a yellow oil (6.6 g, 99%).

Workup

  1. washWashed with water
  2. dry with materialdried the organic layer over MgSO4
  3. filtrationFiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0b9309b8c90e429e955b3d884412c611
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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