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

HRID 1614377ノート

反応式

HRID 1614377 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 62652Cuprous chloride触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-93d71036b5d841d4a6356a5085ee8e0d
出典データセット
uspto-grants-1993_03
特許番号
US05196586

反応ノート

読み込み中…