Dimethyl Sulfoxide → 7-Formylnaphthalene-2-carbonitrile

HRID 362499Notes

Reaction equation

HRID 362499 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]#[N:14])=[CH:10]2)=[CH:5][CH:4]=1.CS(C)=[O:17]>F[B-](F)(F)F.[Ag+]>[CH:2]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]#[N:14])=[CH:10]2)=[CH:5][CH:4]=1)=[O:17]

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 98377487-(Bromomethyl)-2-naphthonitrile

Product 1

HCID 153921967-Formylnaphthalene-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 159722Silver tetrafluoroborateCatalyst

Procedure

Silver tetrafluoroborate (1,168 mg) was suspended in 6 ml of dimethyl sulfoxide, 1,230 mg of 7-Bromomethyl-2-naphthalenecarbonitrile was added to the suspension, and the mixture was stirred at room temperature for 14 hours. The reaction solution was filtered, water was added to the mother liquid, and the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, and then evaporated. The resulting residue was purified by silica gel column chromatography using a mixture of hexane and ethyl acetate as the eluent to give 543 mg of 7-formyl-2-naphthalenecarbonitrile in the form of white solid.

Workup

  1. filtrationThe reaction solution was filtered
  2. additionwater was added to the mother liquid
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe resulting residue was purified by silica gel column chromatography
  8. additiona mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-294471f9d88341a3911b311e9d80b976
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

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