Water → 2,6-Difluoro-4-formylbenzonitrile

HRID 505011Notes

Reaction equation

HRID 505011 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.

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-bb035ad1785a4d0bbc57a768d2cc98f3
Source dataset
uspto-grants-2010_08
Patent number
US07781424B2

Reaction notes

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