Methane → 2'-Fluoro-5'-(2-oxoacetyl)biphenyl-2-carbonitrile

HRID 1064263

Reaction equation

HRID 1064263 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([F:18])=[C:8]([C:10]2[C:11]([C:16]#[N:17])=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:9]=1)(=[O:3])[CH3:2].O.[Se](=O)=[O:21].C>O1CCOCC1>[F:18][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH:2]=[O:21])=[CH:9][C:8]=1[C:10]1[C:11]([C:16]#[N:17])=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 962WaterHCID 24007Selenium DioxideHCID 222736025'-Acetyl-2'-fluorobiphenyl-2-carbonitrile

Product 1

HCID 222735942'-Fluoro-5'-(2-oxoacetyl)biphenyl-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5′-Acetyl-2′-fluorobiphenyl-2-carbonitrile (0.31 g, 1.3 mmol) was suspended in 1,4-dioxane (4.75 ml) and water (0.25 ml) and warmed to 60° C. to solubilise the starting material. The solution was then cooled to ambient temperature, selenium dioxide (0.17 g, 1.55 mmol) added and the mixture heated under reflux for 2 h. The mixture was then allowed to cool to 60° C., activated charcoal (1 g) added and the mixture stirred for 30 min. The mixture was then allowed to cool to ambient temperature, filtered through a glass fibre filter paper and the solid washed with 1,4-dioxane (10 ml) and the filtrate evaporated to give crude 2′-fluoro-5′-(2-oxoacetyl)biphenyl-2-carbonitrile which was used without further purification in the next step.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 h
  3. temperatureto cool to 60° C.
  4. temperatureto cool to ambient temperature
  5. filtrationfiltered through a glass fibre
  6. filtrationfilter paper
  7. washthe solid washed with 1,4-dioxane (10 ml)
  8. customthe filtrate evaporated

Sources & evidence

ORD record
ord-6088685a4c1046deb56f1eebd6f7d5ef
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Linked notes

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