Benzene → 1-[3-(N-methylamino)phenyl]-4-[3,5-bis(trifluoromethyl)phenyl]-1,3-butadiyne

HRID 1614383Notes

Reaction equation

HRID 1614383 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]#[CH:12])[CH:6]=[CH:7][CH:8]=1.[F:13][C:14]([F:27])([F:26])[C:15]1[CH:16]=[C:17](I)[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1.C1C=CC=CC=1>CN(C)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]Cl>[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][C:11]#[C:12][C:17]2[CH:18]=[C:19]([C:21]([F:24])([F:22])[F:23])[CH:20]=[C:15]([C:14]([F:13])([F:27])[F:26])[CH:16]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 241BenzeneHCID 6309701-Iodo-3,5-bis(trifluoromethyl)benzeneHCID 197738121-[3-(N-methylamino)phenyl]-1,3-butadiyne

Product 1

HCID 197738111-[3-(N-methylamino)phenyl]-4-[3,5-bis(trifluoromethyl)phenyl]-1,3-butadiyneYield 76.7%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1146TrimethylamineSolvent

Procedure

320 mg of the thus-obtained 1-[3-(N-methylamino)phenyl]-1,3-butadiyne and 700 mg of 3,5-bis(trifluoromethyl) iodobenzene were dissolved in 30 ml of trimethylamine in an atmosphere of argon, and 14 mg of bis(triphenylphosphine)palladium (II) chloride and 4 mg of copper (I) chloride were then rapidly added to the reaction mixture. After the solution had been stirred at room temperature for 13 hours, 50 ml of benzene were added thereto, and the solvent was then evaporated. The residue was neutralized by 1N hydrochloric acid and subjected to extraction with 50 ml of benzene three times. The organic layer was then dried over magnesium sulfate, and the solvent was evaporated. The residue was then purified by silica-gel chromatography using a mixture of hexane and benzene as an eluent to obtain 580 mg of 1-[3-(N-methylamino)phenyl]-4-[3,5-bis(trifluoromethyl)phenyl]-1,3-butadiyne. This compound was a yellowish green crystal having a melting point of from 75° to 76° C.

Workup

  1. additionwere then rapidly added to the reaction mixture
  2. customthe solvent was then evaporated
  3. extractionsubjected to extraction with 50 ml of benzene three times
  4. dry with materialThe organic layer was then dried over magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was then purified by silica-gel chromatography
  7. additiona mixture of hexane and benzene as an eluent

Sources & evidence

ORD record
ord-ea10c499d3144b4296bd0e2bd8b6895a
Source dataset
uspto-grants-1993_03
Patent number
US05196586

Reaction notes

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