N-Methylmorpholine N-oxide monohydrate → 5-(3,5-Difluorobenzoyl)-2-fluorobenzonitrile

HRID 571889Notes

Reaction equation

HRID 571889 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:19])[C:10]2[CH:11]=[CH:12][C:13]([F:18])=[C:14]([CH:17]=2)[C:15]#[N:16])[CH:5]=[C:6]([F:8])[CH:7]=1.O.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[C:9]([C:10]1[CH:11]=[CH:12][C:13]([F:18])=[C:14]([CH:17]=1)[C:15]#[N:16])=[O:19]

Participants

5

Reactant 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 686715605-((3,5-Difluorophenyl)(hydroxy)methyl)-2-fluorobenzonitrile

Product 1

HCID 686714725-(3,5-Difluorobenzoyl)-2-fluorobenzonitrileYield 77%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-[(3,5-Difluoro-phenyl)-hydroxy-methyl]-2-fluoro-benzonitrile (2.68 g, 10.2 mmol), 4-methylmorpholine N-oxide monohydrate (2.02 g, 15 mmol) and tetrapropylammonium perruthenate (35 mg, 0.1 mmol) in dry dichloromethane (50 mL) was stirred at room temperature for 2 hours. The reaction mixture was evaporated and the residue redissolved in ethyl acetate. The organic phase was washed with 10% sodium bisulphite and saturated ammonium chloride, dried and evaporated. Purification of the crude by chromatography over silica gel (EtOAc/hexane) afforded 2.05 g of the title compound (77% yield).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue redissolved in ethyl acetate
  3. washThe organic phase was washed with 10% sodium bisulphite and saturated ammonium chloride
  4. customdried
  5. customevaporated
  6. customPurification of the crude by chromatography over silica gel (EtOAc/hexane)

Sources & evidence

ORD record
ord-ba59fb0f808f42d1872c33652fb8f193
Source dataset
uspto-grants-2015_05
Patent number
US09029356B2

Reaction notes

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