Phenol → 4-Bromo-2-phenoxybenzonitrile

HRID 1987938Notes

Reaction equation

HRID 1987938 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13](F)[CH:12]=1.[OH-].[Na+]>CN(C=O)C>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 574366654-Bromo-2-phenoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (12 g, 300 mmol) (60% by wt) was weighed into a flask and washed free of oil with several hexane rinsings. The hexanes were decanted and discarded and DMF was added to the flask. A solution of phenol (23.5 g, 250 mmol) in DMF (100 mL) was added dropwise and the mixture was stirred at room temperature. To the mixture was added a solution of 4-bromo-2-fluoro-benzonitrile (50 g, 250 mmol, 100 mL DMF), dropwise. Upon complete addition, the reaction was refluxed for 20 h. The reaction was cooled to room temperature and poured into cold 1 N NaOH. A fine, tan precipitate formed and was collected by vacuum filtration to give Compound 5c. MS m/z (MH+) 277.

Workup

  1. washwashed free of oil with several hexane rinsings
  2. customThe hexanes were decanted
  3. additionDMF was added to the flask
  4. additionUpon complete addition
  5. temperaturethe reaction was refluxed for 20 h
  6. temperatureThe reaction was cooled to room temperature
  7. customA fine, tan precipitate formed
  8. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-abfea0510356481e9f8595821d24de8d
Source dataset
uspto-grants-2009_06
Patent number
US07553850B2

Reaction notes

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