4-Bromoaniline → 1-(4-Bromophenyl)-2,5-diphenylpyrrole

HRID 1837392

Reaktionsgleichung

Reaktionsgleichung von HRID 1837392
[C:1]1([C:7]#[C:8][C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1>C(Cl)(Cl)Cl.[Cu]Cl>[Br:17][C:18]1[CH:24]=[CH:23][C:21]([N:22]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][CH:9]=[C:10]2[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:20][CH:19]=1

Komponenten

5

Edukt 2

HCID 78074-BromoanilineHCID 701741,4-Diphenyl-1,3-butadiyne

Produkt 1

HCID 17751381-(4-Bromophenyl)-2,5-diphenylpyrroleAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, 15 g (74 mmol) of 1,4-di-phenylbutadiyne, 12.76 g (74 mmol) of p-bromoaniline and 1.84 g (18 mmol) copper(I) chloride were put into 500 ml round-bottomed flask, and the resulting mixture was reacted at 150° C. for 5 hours while stirring. After the reaction was completed, the reaction mixture was cooled down to room temperature, dissolved in chloroform and then washed with 5% hydrochloric acid several times. The combined organic extract was washed with water several times and then dried with anhydrous magnesium sulfate. The solvent was removed to obtain solid, which was recrystallized from ethyl acetate to give 20.4 g (73.5%) white solid having a melting point of 218-219° C.

Aufarbeitung

  1. customthe resulting mixture was reacted at 150° C. for 5 hours
  2. washwashed with 5% hydrochloric acid several times
  3. extractionThe combined organic extract
  4. washwas washed with water several times
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was removed
  7. customto obtain solid, which
  8. customwas recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-efd9c390287548859a18f29cf5d1b609
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06780950B2

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