Water → 4-Bromo-2,6-difluorobenzonitrile

HRID 2054901Notes

Reaction equation

HRID 2054901 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[C:5]([C:6]([NH2:8])=O)=[C:4]([F:12])[CH:3]=1.N1C(Cl)=NC(Cl)=NC=1Cl.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([F:12])[C:5]([C:6]#[N:8])=[C:9]([F:11])[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 596566824-BroMo-2,6-difluorobenzaMide, 96%

Product 1

HCID 27569164-Bromo-2,6-difluorobenzonitrileYield 86.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the above benzamide intermediate (9.4 g, 40 mmol) in DMF (15 mL) was added cyanuric chloride (7.24 g, 40 mL) at 0° C. The reaction was stirred at 0° C. for 3 h. Water was added slowly to the reaction and it was extracted with CH2Cl2 (3×100 mL). The solvent was washed with brine and dried over Na2SO4. The solvent was removed to give 4-bromo-2,6-difluorobenzonitrile (7.57 g, 86.9%).

Workup

  1. extractionwas extracted with CH2Cl2 (3×100 mL)
  2. washThe solvent was washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-cefb165d6ae74070829d19c8c1122260
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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