Formic Acid → 5-(4-Fluoro-benzoyl)-2-methylsulfonylnaphthalene

HRID 1738308Notes

Reaction equation

HRID 1738308 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(O)=O.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.[Cl-].[Na+].O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:17]=[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

8

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 221256945-(4-Fluorobenzoyl)-6-trifluoromethylsulfonyloxy-2-methylsulfonylnaphthalene

Product 1

HCID 154346195-(4-Fluoro-benzoyl)-2-methylsulfonylnaphthaleneYield 48.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 5-(4-fluorobenzoyl)-6-trifluoromethylsulfonyloxy-2-methylsulfonylnaphthalene (0.3 g, 0.63 mmol), [prepared as described in step 1 above], formic acid (0.096 ml, 2.5 mmol), triethylamine(0.36 ml, 2.5 mmol), palladium acetate (14 mg, 0.06 mmol), and 1,3-bis(diphenylphosphino)propane (0.10 g, 0.03 mmol) in DMF (10 ml) was stirred at room temperature. After 16 h, the reaction mixture was poured into brine and extracted into ethyl acetate. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by flash chromatography (gradient elution 10-30% ethyl acetate/hexanes) and then recrystallized from ethyl acetate -hexanes to give 0.1 g of 5-(4-fluoro-benzoyl)-2-methylsulfonylnaphthalene as a solid (48% yield).

Workup

  1. extractionextracted into ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography (gradient elution 10-30% ethyl acetate/hexanes)
  6. customrecrystallized from ethyl acetate -hexanes

Sources & evidence

ORD record
ord-d6d57dff52064c0a8e8f325035b835ac
Source dataset
uspto-grants-1999_10
Patent number
US05962531

Reaction notes

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