Sodium Hydroxide → 3-(2,3-Difluorophenyl)propanenitrile

HRID 2374729Notes

Reaction equation

HRID 2374729 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11](O)=O.C(Cl)(=O)C(Cl)=O.S(N)([NH2:23])(=O)=O.[OH-].[Na+]>ClCCl.CN(C=O)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]#[N:23]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 82267SulfamideHCID 37993363-(2,3-difluorophenyl)propanoic Acid

Product 1

HCID 184490163-(2,3-Difluorophenyl)propanenitrileYield 100.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2,3-difluorophenyl)-propionic acid (A1) (6.83 g, 36 mmol) in anhydrous dichloromethane (50 ml) containing a few drops of DMF was added oxalyl chloride (6.4 ml, 73 mmol) at 0° C. under argon. The solution was stirred at ambient temperature for 2 h and the solvent removed in vacuo. The residue was dissolved in sulfolane (30 ml) and added to sulfamide (4.23 g, 44 mmol) and the mixture heated at 120° C. for 3 h. The brown solution was cooled, poured into 2M sodium hydroxide solution (300 ml) and extracted with ether. The combined extracts were washed with water, dried (MgSO4) and evaporated to give the title compound as a brown oil (6.04 g, 98%). 1H-NMR (CDCl3) δ 2.68 (2H, t), 3.04 (2H, t), 7.01-7.15 (3H, m).

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in sulfolane (30 ml)
  3. temperaturethe mixture heated at 120° C. for 3 h
  4. temperatureThe brown solution was cooled
  5. extractionextracted with ether
  6. washThe combined extracts were washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-8fe9811955454e82aae33139ae192141
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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