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Benzene → 1-(4-Methoxyphenyl)-4-[2,5-bis(trifluoromethyl)phenyl]-1,3-butadiyne

HRID 1614377
Notes
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Reaction equation

HRID 1614377 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]#[CH:12])=[CH:5][CH:4]=1.[F:13][C:14]([F:27])([F:26])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=1I.C1C=CC=CC=1>C(N(CC)CC)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][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]#[C:12][C:16]2[CH:17]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:19]=[CH:20][C:15]=2[C:14]([F:13])([F:26])[F:27])=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 241BenzeneHCID 27790862-Iodo-1,4-bis(trifluoromethyl)benzeneHCID 105111001-(4-Methoxyphenyl)-1,3-butadiyne

Product 1

HCID 197738101-(4-Methoxyphenyl)-4-[2,5-bis(trifluoromethyl)phenyl]-1,3-butadiyneYield 61.7%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalyst
HCID 6102075
Dichlorobis(triphenylphosphine)palladium
Catalyst
HCID 8471TriethylamineSolvent

Procedure

1100 mg of the 1-(4-methoxyphenyl)-1,3-butadiyne obtained and 2700 mg of 2,5-bis(trifluoromethyl) iodobenzene were then dissolved in 50 ml of triethylamine, and 50 mg of bis(triphenylphosphine)palladium (II) chloride and 14 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 to the reaction mixture, and the precipitates produced were then filtered off. After the solvent had been evaporated, the residue was neutralized by 1N hydrochloric acid and subjected to extraction with 50 ml of benzene three times. The organic layer was dried over magnesium sulfate, and the solvent was then evaporated. The residue was purified by silica-gel column chromatography using hexane as an eluent to obtain 1600 mg of 1-(4-methoxyphenyl)-4-[2,5-bis(trifluoromethyl)phenyl]-1,3-butadiyne. This compound was a needle-like white crystal having a melting point of from 86° to 88° C.

Workup

  1. customthe precipitates produced
  2. filtrationwere then filtered off
  3. customAfter the solvent had been evaporated
  4. extractionsubjected to extraction with 50 ml of benzene three times
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was then evaporated
  7. customThe residue was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-93d71036b5d841d4a6356a5085ee8e0d
Source dataset
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05196586

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes