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

HRID 1501974Notes

Reaction equation

HRID 1501974 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-ff9948fc7ffc45e4abc644cc80a1037c
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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