Ammonia → 4-Fluoro-2-methylbenzonitrile

HRID 1593383Notes

Reaction equation

HRID 1593383 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-52c469bddda74fd191a6b38315ab9ac9
Source dataset
uspto-grants-2007_11
Patent number
US07297698B2

Reaction notes

Loading…