Dimethylformamide → 2-Chloro-4-(trifluoromethoxy)benzonitrile

HRID 2099308Notes

Reaction equation

HRID 2099308 reaction equation
FC(S(O[C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=1[Cl:20])(=O)=O)(F)F.[CH3:21][N:22](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:20][C:10]1[CH:11]=[C:12]([O:15][C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:14][C:9]=1[C:21]#[N:22]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 57643424HCID 57643424, compound

Product 1

HCID 668610192-Chloro-4-(trifluoromethoxy)benzonitrile

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

3.00 g of the compound from Example 2A are dissolved in 12 ml of degassed DMF with 2.04 g of zinc cyanide and 1.00 g of tetrakis(triphenylphosphine)palladium and the mixture is heated under argon at 120° C. for 2 h. After cooling, the reaction mixture is diluted with ethyl acetate and extracted by shaking twice with a saturated sodium hydrogen carbonate solution and then with a saturated sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated. The residue is purified by silica gel chromatography (cyclohexane/ethyl acetate 10:1).

Workup

  1. temperatureAfter cooling
  2. extractionextracted
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel chromatography (cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-b2233d8931474219aa4d8a4f0da7873b
Source dataset
uspto-grants-2009_08
Patent number
US07569563B2

Reaction notes

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