Water → 2,6-Difluoro-4-formylbenzonitrile

HRID 917293Notes

Reaction equation

HRID 917293 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH:10](S(C)=O)SC)[CH:7]=[C:6]([F:16])[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])[CH:7]=[C:6]([F:16])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 21904656HCID 21904656, compound

Product 1

HCID 219046552,6-Difluoro-4-formylbenzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,6-Difluoro-4[(methylsulfinyl)(methylthio)methyl]benzonitrile (2.17 g, 8.32 mmol; see step (i) above) was dissolved in 90 mL of THF and 3.5 mL of concentrated sulfuric acid was added. The mixture was left at room temperature for 3 days and subsequently poured into 450 mL of water. Extraction three times with EtOAc followed and the combined ethereal phase was washed twice with aqueous sodium bicarbonate and with brine, dried (Na2SO4) and evaporated. Yield: 1.36 g (98%). The position of the formyl group was established by 13C NMR. The signal from the fluorinated carbons at 162.7 ppm exhibited the expected coupling pattern with two coupling constants in the order of 260 Hz and 6.3 Hz respectively corresponding to an ipso and a meta coupling from the fluorine atoms.

Workup

  1. extractionExtraction three times with EtOAc
  2. washthe combined ethereal phase was washed twice with aqueous sodium bicarbonate and with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-447bf71e868c4f9faa12da5de3ea6bd5
Source dataset
uspto-grants-2007_09
Patent number
US07273858B2

Reaction notes

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