Dimethylformamide → 4-Fluoro-2-methylbenzonitrile

HRID 2427484Notes

Reaction equation

HRID 2427484 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH3:8])[CH:7]=1.[CH3:10][N:11](C=O)C>[C-]#N.[C-]#N.[Zn+2].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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]#[N:11])=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 27745254-Fluoro-1-iodo-2-methylbenzene

Product 1

HCID 38260554-Fluoro-2-methylbenzonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

5-Fluoro-2-iodotoluene (3 g, 12.7 mmol) was stirred in DMF (40 mL) under argon and Zn(CN)2 (1.94 g, 16.5 mmol) and Pd(PPh3)4 (1.47 g, 1.27 mmol) were added. The reaction was stirred at 80° C. for 1.5 hours. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2-SO4. The solvent was removed under reduced pressure to afford a yellow solid (2.90 g), confirmed by GC MS.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2-SO4
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-18ae5adeb240434593b60ef092f81acb
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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