Acetic Acid → 4-Bromo-3,5-difluorobenzonitrile

HRID 1639192Notes

Reaction equation

HRID 1639192 reaction equation
S(=O)(=O)(O)O.C(O)(=O)C.[C:10]([C:12]1[CH:18]=[C:17]([F:19])[C:15](N)=[C:14]([F:20])[CH:13]=1)#[N:11].O.[BrH:22]>[Cu]Br>[Br:22][C:15]1[C:17]([F:19])=[CH:18][C:12]([C:10]#[N:11])=[CH:13][C:14]=1[F:20]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 962WaterHCID 1118Sulfuric AcidHCID 2804674-Amino-3,5-difluorobenzonitrile

Product 1

HCID 147942904-Bromo-3,5-difluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst

Procedure

4 g of sodium nitride was added to 30 ml of concentrated sulfuric acid and chilled to a temperature of 10° C. and 38 ml of acetic acid was added thereto. 8.9 ml of 4-cyano-2,6-difluoroaniline was added gradually to maintain the solution at a temperature of 20° to 25° C. The reaction mixture was added dropwise to a solution a 10 g of copper (I) bromide dissolved in 30 ml of concentrated hydrobromic acid. After the dropwise addition was completed, the reaction mixture was stirred for one and one half hours at room temperature. Water was added to the reaction mixture, the reaction mixture was extracted with chloroform and washed with water. The organic layer was removed by distillation, and the residue was recrystallized with a mixture of methanol and acetone to yield 6.6 g of 2-bromo-5-cyano-1,3-difluorobenzene.

Workup

  1. additionwas added
  2. temperatureto maintain the solution at a temperature of 20° to 25° C
  3. additionAfter the dropwise addition
  4. extractionthe reaction mixture was extracted with chloroform
  5. washwashed with water
  6. customThe organic layer was removed by distillation
  7. customthe residue was recrystallized with a mixture of methanol and acetone

Sources & evidence

ORD record
ord-c518c4b4842a41ac80315e38abcc318d
Source dataset
uspto-grants-1989_11
Patent number
US04883609

Reaction notes

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