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

HRID 1011213Notes

Reaction equation

HRID 1011213 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 of 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 solution 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). 880 mg (44% of theory) of the title compound are obtained.

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-ea64c47412024f5293c581585e9d9ed7
Source dataset
uspto-grants-2011_07
Patent number
US07977349B2

Reaction notes

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