MAGNESIUM SILICATE (synthetic) → 3'-Cyano-4'-fluoroacetophenone

HRID 2175800Notes

Reaction equation

HRID 2175800 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]([OH:12])[CH3:11])=[CH:6][C:3]=1[C:4]#[N:5].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[O-][Si]([O-])=O.[Mg+2]>C(Cl)Cl.CCOCC>[C:10]([C:7]1[CH:8]=[CH:9][C:2]([F:1])=[C:3]([CH:6]=1)[C:4]#[N:5])(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 2724130Cornforth reagentHCID 577800282-Fluoro-5-(1-hydroxyethyl)benzonitrile

Product 1

HCID 224583893'-Cyano-4'-fluoroacetophenone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-5-(1-hydroxyethyl)benzonitrile (0.80 g, 4.8 mmol) was dissolved in DCM (50 mL). To this mixture was added pyridinium dichromate (2.73 g, 7.27 mmol) and the mixture was stirred at RT overnight. Florisil (26 g) was added to the reaction mixture which was then diluted with 50 mL of ether and filtered through a pad of Celite. The filtrate was evaporated to dryness and the residue was purified by MPLC through a 120 g Redi-sep column, eluting with 0-100% EtOAc/hexane to yield 5-acetyl-2-fluorobenzonitrile.

Workup

  1. filtrationfiltered through a pad of Celite
  2. customThe filtrate was evaporated to dryness
  3. customthe residue was purified by MPLC through a 120 g Redi-sep column
  4. washeluting with 0-100% EtOAc/hexane

Sources & evidence

ORD record
ord-925867fef5054f9198a359d1e723bc2d
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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