2-Fluorobenzonitrile → HCID 67210811, compound

HRID 1179115Notes

Reaction equation

HRID 1179115 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N+](=[C:12]1[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]1=[O:19])=[N-]>FC1C(F)=C(F)C(F)=C(F)C=1F.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]1[O:18][C:17]2[CH2:16][CH2:15][CH2:14][C:13](=[O:19])[C:12]=2[N:5]=1

Participants

5

Reactant 2

HCID 678552-FluorobenzonitrileHCID 110624492-diazocyclohexane-1,3-dione

Product 1

HCID 67210811HCID 67210811, compound

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 9805HexafluorobenzeneSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of rhodium acetate (32 mg, 72 μmol) and 2-fluorobenzonitrile (2.31 ml; 22 mmol) in perfluorobenzene (5 ml) is treated at 60° C. dropwise by a solution of diazocyclohexanedione (obtained in Stage 66.1; 1 g; 7.24 mmol) in 5 ml of perfluorobenzene. The reaction medium is maintained at 60° C. until exhaustion of the release of nitrogen (1 hour; TLC on SiO2: 2% MeOH/CH2Cl2). After cooling down to ambient temperature and filtration, the solvent of the filtrate is evaporated. The residue is purified by chromatography (SiO2: AcOEt/heptane: 1/1) in order to produce a light yellow powder.

Workup

  1. temperatureAfter cooling down to ambient temperature
  2. filtrationfiltration
  3. customthe solvent of the filtrate is evaporated
  4. customThe residue is purified by chromatography (SiO2: AcOEt/heptane: 1/1) in order
  5. customto produce a light yellow powder

Sources & evidence

ORD record
ord-3ea6d810023345b3bcecfdeff32a46d6
Source dataset
uspto-grants-2007_10
Patent number
US07279467B2

Reaction notes

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