Benzene → 2,3,4,6-Tetrafluorobiphenyl

HRID 485543Notes

Reaction equation

HRID 485543 reaction equation
[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[C:5]([F:11])[C:3]=1N.[CH:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N(OC(C)(C)C)=O>CCCCCCC>[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[C:5]([F:11])[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 10906Tert-Butyl nitriteHCID 1230482,3,4,6-Tetrafluoroaniline

Product 1

HCID 128530492,3,4,6-Tetrafluorobiphenyl

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

A stirred solution of 2,3,4,6-tetrafluoroaniline (50 g, 0.30 mole) in benzene (236.6 g, 3.03 mole) was heated under reflux. During a 45 minute period, t-butyl nitrite (46.8 g, 0.455 mole) was added to the reaction mixture. After complete addition the mixture was heated at reflux for 23/4 hours. n-Heptane (1 l) was added, and the solvent was distilled from the reaction flask until a head temperature of 101° was reached. The pot residue was cooled and subjected to column chromatography on silica gel, elution first with n-heptane, then toluene, to give 2,3,4,6-tetrafluoro-[1,1'-biphenyl] (mp, 89°-90°).

Workup

  1. temperatureunder reflux
  2. additionAfter complete addition the mixture
  3. temperaturewas heated
  4. temperatureat reflux for 23/4 hours
  5. distillationthe solvent was distilled from the reaction flask until a head temperature of 101°
  6. temperatureThe pot residue was cooled
  7. washsubjected to column chromatography on silica gel, elution first with n-heptane

Sources & evidence

ORD record
ord-734e0a729ac94a4fa9f2e04e70fc59f9
Source dataset
uspto-grants-1985_08
Patent number
US04536591

Reaction notes

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