Water → 2,5-Difluoro-4-formylbenzonitrile

HRID 1246678Notes

Reaction equation

HRID 1246678 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH:10](S(C)=O)SC)[C:7]([F:16])=[CH:6][C:3]=1[C:4]#[N:5].S(=O)(=O)(O)[OH:18].O>C1COCC1>[F:1][C:2]1[CH:9]=[C:8]([CH:10]=[O:18])[C:7]([F:16])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 219046172,5-Difluoro-4-[(methylsulfinyl)(methylthio)methyl]benzonitrile

Product 1

HCID 219046262,5-Difluoro-4-formylbenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,5-Difluoro-4[(methylsulfinyl)(methylthio)methyl]benzonitrile (2.8 g, 0.0107 mol; see step (i) above) was dissolved in 100 mL of THF and 6.5 g of concentrated sulfuric acid was added. The mixture was left at room temperature for 6 days and subsequently poured into 500 mL of water. Extraction three times with diethyl ether followed and the combined ethereal phase was washed several times with water, dried (Na2SO4) and evaporated. The crude product was flash chromatographed on silica gel using heptane:EtOAc (8:2). Yield: 1.2 g (67%). The position of the formyl group was established by use of 13C NMR. The carbon signals from the fluorinated carbons at 160.1 and 158.4 respectively were doublets and not quartets, which they would have been if the formyl group had been in the 2-position.

Workup

  1. extractionExtraction three times with diethyl ether
  2. washthe combined ethereal phase was washed several times with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-4648888a0a4e4977bd328bd65ed7f240
Source dataset
uspto-grants-2006_10
Patent number
US07129233B2

Reaction notes

Loading…