Toluene → 1,4-Benzenedicarbonitrile, 2-fluoro-

HRID 1862013Notes

Reaction equation

HRID 1862013 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.C1(C)C=CC=CC=1.[Cl-].[NH4+].[CH3:20][N:21](C=O)C>[C-]#N.[Zn+2].[C-]#N>[F:10][C:4]1[CH:3]=[C:2]([C:20]#[N:21])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 1211941,4-Benzenedicarbonitrile, 2-fluoro-

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

A solution of 4-bromo-2-fluorobenzonitrile (20 g, 100 mmol), zinc cyanide (7 g, 60 mmol) and tetrakis(triphenyl-phosphine)palladium (4.6 g, 4 mmol) in DMF (100 mL) was heated at 80° C. for 4 hr. Toluene (300 mL) and saturated aqueous ammonium chloride (300 mL) were added and the layers were separated. The organic layer was washed once with saturated aqueous ammonium chloride and twice with brine. The organic phase was dried (MgSO4), filtered and concentrated. The product was purified by silica gel chromatography, eluting with a gradient of hexanes to 30% EtOAc/hexanes (11 g, 75%).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed once with saturated aqueous ammonium chloride and twice with brine
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by silica gel chromatography
  7. washeluting with a gradient of hexanes to 30% EtOAc/hexanes (11 g, 75%)

Sources & evidence

ORD record
ord-b8cf56e12ed04d6591b955df6f8ee7a0
Source dataset
uspto-grants-2003_03
Patent number
US06534650B2

Reaction notes

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