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

HRID 1837392Notes

Reaction equation

HRID 1837392 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 17751381-(4-Bromophenyl)-2,5-diphenylpyrroleYield 73.7%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6212ChloroformSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-efd9c390287548859a18f29cf5d1b609
Source dataset
uspto-grants-2004_08
Patent number
US06780950B2

Reaction notes

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