Dimethylformamide → 2,4,6-Trichlorobenzonitrile

HRID 252144Notes

Reaction equation

HRID 252144 reaction equation
I[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[Cl:10].[CH3:11][N:12](C=O)C>C1(C)C=CC=CC=1.[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:10][C:3]1[CH:4]=[C:5]([Cl:9])[CH:6]=[C:7]([Cl:8])[C:2]=1[C:11]#[N:12]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 2320541,3,5-Trichloro-2-iodobenzene

Product 1

HCID 5221792,4,6-TrichlorobenzonitrileYield 84%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

Add 1-iodo-2,4,6-trichlorobenzene (1500 mg, 4.88 mmol), zinc cyanide (345 mg, 2.94 mmol) and tetrakis(triphenylphosphine)palladium(0) (282 mg, 0.244 mmol) to anhydrous DMF (30 mL). Heat to 85° C. overnight. Cool to room temperature, dilute with toluene, wash with 2 N ammonium hydroxide (3×) and saturated aqueous sodium chloride and concentrate. Purify by silica gel chromatography, eluting with hexanes/dichloromethane to give 2,4,6-trichlorobenzonitrile (850 mg, 84%): 1H NMR (400 MHz, CDCl3) δ 7.76 (s, 1H), 7.65 (s, 1H).

Workup

  1. temperatureCool to room temperature
  2. washwash with 2 N ammonium hydroxide (3×) and saturated aqueous sodium chloride
  3. concentrationconcentrate
  4. customPurify by silica gel chromatography
  5. washeluting with hexanes/dichloromethane

Sources & evidence

ORD record
ord-bcba059513ab48168ac1f4d8f52ee5d0
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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