Selenium Dioxide → 4,2'-Difluoro-5'-(2-oxoacetyl)biphenyl-2-carbonitrile

HRID 1064265Notes

Reaction equation

HRID 1064265 reaction equation
[Se](=O)=[O:2].[C:4]([C:7]1[CH:8]=[CH:9][C:10]([F:22])=[C:11]([C:13]2[C:14]([C:20]#[N:21])=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[CH:12]=1)(=[O:6])[CH3:5]>O1CCOCC1.O.O1CCOCC1>[F:19][C:16]1[CH:15]=[C:14]([C:20]#[N:21])[C:13]([C:11]2[CH:12]=[C:7]([C:4](=[O:6])[CH:5]=[O:2])[CH:8]=[CH:9][C:10]=2[F:22])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 222735995'-Acetyl-4,2'-difluorobiphenyl-2-carbonitrile

Product 1

HCID 222735874,2'-Difluoro-5'-(2-oxoacetyl)biphenyl-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Selenium dioxide (0.556 g, 5.00 mmol) dissolved in 1,4dioxane:water (4:1, 5 ml) was added in one portion to 5′-acetyl-4,2′-difluorobiphenyl-2-carbonitrile (0.92 g, 3.58 mmol) in 1,4-dioxane (10 ml) and the mixture heated at reflux for 18 h. The reaction was allowed to cool to room temperature, filtered and the filtrate evaporated to give an orange-coloured glassy solid which was used without further purification (0.97 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 h
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. customto give an orange-coloured glassy solid which
  6. customwas used without further purification (0.97 g)

Sources & evidence

ORD record
ord-9d072019c3c84985bee2148115ea4429
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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