Sodium Hydroxide → 4-(3-Fluoro-4-hydroxybenzoyl)benzonitrile

HRID 1683447Notes

Reaction equation

HRID 1683447 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[O:18]C)[C:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[O:6].B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[OH:18])[C:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 19043702HCID 19043702, compound

Product 1

HCID 190437654-(3-Fluoro-4-hydroxybenzoyl)benzonitrileYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 50 g of 4-(3-fluoro-4-methoxy-benzoyl)benzonitrile in 550 ml of methylene chloride is treated with 70 ml of BBr3 at 5° C. and stirred at room temperature. 1 l of 1M NaOH is added dropwise while cooling with ice. Then, the mixture is extracted with saturated aqueous NH4Cl solution and methylene chloride. The organic phase is washed with water and dried. After recrystallization from ether, there are obtained 34 g of 4-(3-fluoro-4-hydroxy-benzoyl)-benzonitrile, m.p. 168.5°-169.5° C.

Workup

  1. temperaturewhile cooling with ice
  2. extractionThen, the mixture is extracted with saturated aqueous NH4Cl solution and methylene chloride
  3. washThe organic phase is washed with water
  4. customdried
  5. customAfter recrystallization from ether, there

Sources & evidence

ORD record
ord-3ede8702af6345c392830e26176ca46a
Source dataset
uspto-grants-1997_06
Patent number
US05637771

Reaction notes

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