2-Bromo-4-fluorobenzonitrile → 2-Bromo-4-hydroxybenzonitrile

HRID 716805Notes

Reaction equation

HRID 716805 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C[Si](C)(C)[O-:13].[K+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[C:8]([OH:13])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 2

HCID 1189392-Bromo-4-fluorobenzonitrileHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 130422512-Bromo-4-hydroxybenzonitrileYield 101%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-bromo-4-fluoro-benzonitrile (2000 mg, 9.9995 mmol) in DMF (20 mL), potassium trimethylsilanolate (2565.7 mg, 19.999 mmol) was added portionwise and the reaction mixture stirred at room temperature for 1 h. The mixture was diluted with ethyl acetate (100 ml), washed with an aqueous saturated solution of ammonium chloride (100 ml) and brine (3×100 ml), dried over sodium sulphate and concentrated under vacuum to give the title compound (2000 mg) which was used in the next step without purification.

Workup

  1. washwashed with an aqueous saturated solution of ammonium chloride (100 ml) and brine (3×100 ml)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b3fefedbb91845ceb8cf376ac36fbb29
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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