HCID 67252430, compound → 3-(2-Fluorophenyl)propanenitrile

HRID 2427549Notes

Reaction equation

HRID 2427549 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]#[N:11].[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]#[N:11]

Participants

5

Reactant 2

HCID 67252430HCID 67252430, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 390583363-(2-Fluorophenyl)propanenitrileYield 96%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of the cis/trans mixture of 3-(2-fluorophenyl)acrylonitrile (9.36 g) in ethanol (100 mL) was treated with Pearlman's catalyst (palladium hydroxide, 1 g, 20% Pd by wt. dry) and the mixture shook vigorously under 60 p.s.i. hydrogen for 30 minutes. The mixture was filtered and the filtrate concentrated to afford 3-(2-fluorophenyl) propionitrile (9.11 g). GC/MS gave: m/z (rel.int.) 149 (M+, 19), 109 (100) and 83 (15).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-e35fff383fde49f0a3b8942581f74f48
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…