Water → 4-Bromo-2,6-difluorobenzonitrile

HRID 2367310Notes

Reaction equation

HRID 2367310 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 368.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-bromo-2,6-difluorobenzamide (9 5 g) in DMF (1 L) at 0° C. was added cyanuric chloride (82 g) slowly, and the reaction mixture was stirred at 0° C. for 4 hours. Water (5 L) was added slowly to the reaction, and it was extracted with EtOAc (2 L). The organic layer was separated, dried over MgSO4, filtered and evaporated under vacuum to afford the crude product, which was purified by chromatography (SiO2, 300-400 mesh, petroleum ether:EtOAc=200:1) to provide 47 g of pure title compound and 17 g of impure title compound. 1H NMR (300 MHz, DMSO-d6): δ 7.90 (m, 2H).

Workup

  1. extractionwas extracted with EtOAc (2 L)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customto afford the crude product, which
  7. customwas purified by chromatography (SiO2, 300-400 mesh, petroleum ether:EtOAc=200:1)

Sources & evidence

ORD record
ord-bd470f310e6e46cca245fbdc04cf9fbb
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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