4-ethynyl-2-fluorobenzonitrile → HCID 20682300, compound

HRID 906843Notes

Reaction equation

HRID 906843 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([F:11])[CH:4]=1)#[CH:2].[H][H]>CCOC(C)=O.[Pd]>[CH2:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([F:11])[CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 196905364-ethynyl-2-fluorobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 20682300HCID 20682300, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-ethynyl-2-fluoro-benzonitrile (1.29 g, 8.9 mmol) in EtOAc (30 mL) was placed in a Parr pressure bottle and palladium on carbon (130 mg of 10% on carbon) was added. The bottle was placed on the Parr hydrogenation apparatus and shaken under 10 psi of hydrogen pressure. After shaking for two hours the black suspension was filtered through a pad of Celite. The pad was washed thoroughly with EtOAc, and the combined filtrates were concentrated under reduced pressure. The residue was taken up in toluene and concentrated under reduced pressure to afford 4-ethyl-2-fluoro-benzonitrile (1.19 g, 89% yield). 1H-NMR (400 MHz, CDCl3): δ 7.55-7.50 (1H, m), 7.11-7.03 (2H, m), 2.72 (2H, q, J=7.6 Hz), 1.26 (3H, t, J=7.6 Hz).

Workup

  1. additionwas added
  2. filtrationwas filtered through a pad of Celite
  3. washThe pad was washed thoroughly with EtOAc
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-97948508ef634f9a92e297135e962e38
Source dataset
uspto-grants-2011_09
Patent number
US08013001B2

Reaction notes

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