Potassium Cyanide → 5-(4-Fluorobenzoyl)-6-cyano-2-methylsulfonylnaphthalene

HRID 1738310Notes

Reaction equation

HRID 1738310 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([C:8]2[C:17](OS(C(F)(F)F)(=O)=O)=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:13]3)=[O:7])=[CH:4][CH:3]=1.[C-:32]#[N:33].[K+]>O1CCOCC1.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:17]([C:32]#[N:33])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:13]3)=[O:7])=[CH:30][CH:31]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 221256945-(4-Fluorobenzoyl)-6-trifluoromethylsulfonyloxy-2-methylsulfonylnaphthalene

Product 1

HCID 99284855-(4-Fluorobenzoyl)-6-cyano-2-methylsulfonylnaphthaleneYield 63.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 5-(4-fluorobenzoyl)-6-trifluoromethylsulfonyloxy-2-methylsulfonylnaphthalene (2.5 g, 5.2 mmol) [prepared as described in step 1 above,], potassium cyanide (0.41 g, 6.3 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.30 g, 0.26 mmol) in dioxane (50 ml) was heated at reflux under argon. After 16 h, the reaction mixture was cooled to RT, poured into brine, and the product was extracted into ethyl acetate. The organic layer was dried with sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography (gradient elution, 10-60% ethyl acetate /hexane) and then recrystallized from ethyl acetate-hexane to give 1.16 g of 5-(4-fluorobenzoyl)-6-cyano-2-methylsulfonylnaphthalene as a solid (63% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon
  3. extractionthe product was extracted into ethyl acetate
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (gradient elution, 10-60% ethyl acetate /hexane)
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-bd7f97453ce44c47b1082f92373939cb
Source dataset
uspto-grants-1999_10
Patent number
US05962531

Reaction notes

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