Ammonia → 4-Fluoro-2-methylbenzonitrile

HRID 1445471Notes

Reaction equation

HRID 1445471 reaction equation
C[N:2]([CH:4]=O)C.Br[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[CH3:14].[Cl-].[NH4+].N>[C-]#N.[Zn+2].[C-]#N.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:4]#[N:2])=[C:8]([CH3:14])[CH:9]=1

Participants

9

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 967432-Bromo-5-fluorotoluene

Product 1

HCID 38260554-Fluoro-2-methylbenzonitrile

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×

Conditions

Temperature
140 °C

Procedure

Into 20 ml of DMF was dissolved 10 g of 1-bromo-4-fluoro-2-methylbenzene, and then 0.2 ml of water was added. Then, 3.72 g of zinc cyanide, 484 mg of 1,1′-bis(diphenylphosphino)ferrocene, and 484 mg of tris(dibenzylideneacetone)dipalladium were added thereto under an argon stream, followed by 2 hours of stirring at 140° C. The reaction solution was ice-cooled, ammonium chloride, aqueous ammonia, and water were added thereto, and the resulting solid was collected by filtration. Then, the solid was washed with methanol and the washing liquid was concentrated to obtain 5.7 g of the title compound as a solid.

Workup

  1. temperaturecooled
  2. filtrationthe resulting solid was collected by filtration
  3. washThen, the solid was washed with methanol
  4. concentrationthe washing liquid was concentrated

Sources & evidence

ORD record
ord-d8e12994f89241c3bcd8891020d603dc
Source dataset
uspto-grants-2010_02
Patent number
US07666873B2

Reaction notes

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