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

HRID 1614380Notes

Reaction equation

HRID 1614380 reaction equation
[CH3:1][O: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: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.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 241BenzeneHCID 27790862-Iodo-1,4-bis(trifluoromethyl)benzeneHCID 197738141-(3-Methoxyphenyl)-1,3-butadiyne

Product 1

HCID 197738131-(3-Methoxyphenyl)-4-[2,5-bis(trifluoromethyl)phenyl]-1,3-butadiyneYield 29.6%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

430 mg of the thus-obtained 1-(3-methoxyphenyl)-1,3-butadiyne and 1200 mg of 2,5-bis(trifluoromethyl) iodobenzene were dissolved in 20 ml of triethylamine in an atmosphere of argon, and 21 mg of bis(triphenylphosphine) palladium (II) chloride and 6 mg of copper (I) chloride were rapidly added to the reaction mixture. After the solution had been stirring at room temperature for 13 hours, 30 ml of benzene were added thereto, and the precipitates produced were filtered off. After the solvent had been evaporated, the residue was neutralized by 1N hydrochloric acid and then subjected to extraction with 50 ml benzene three times. The organic layer was dried over magnesium sulfate, and the solvent was then evaporated. The residue was then purified by silica-gel column chromatography using hexane as an eluent to obtain 300 mg of 1-(3-methoxyphenyl)-4-[2,5-bis(trifluoromethyl)phenyl]-1,3-butadiyne. This compound was a slightly yellowish white crystal having a melting point of 37° C.

Workup

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

Sources & evidence

ORD record
ord-326c1212ff2b43ca99903ec5c1457c68
Source dataset
uspto-grants-1993_03
Patent number
US05196586

Reaction notes

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