p-Toluenesulfonic acid → 2-Nitro-4-(1-pyrrolyl)fluorobenzene

HRID 1075447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1075447
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CO[CH:14]1[CH2:18][CH2:17][CH:16](OC)O1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:9]([C:3]1[CH:4]=[C:5]([N:6]2[CH:14]=[CH:18][CH:17]=[CH:16]2)[CH:7]=[CH:8][C:2]=1[F:1])([O-:11])=[O:10]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 677684-Fluoro-3-nitroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Produkt 1

HCID 541021862-Nitro-4-(1-pyrrolyl)fluorobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension of 4-fluoro-3-nitroaniline (20g, 0.13mol) in toluene (200mi) is added 2,5-dimethoxytetrahydrofuran (33ml, 0.26mol) and a catalytic amount of pTSA. The mixture is refluxed for 2.5 hours. After cooling the solvent is removed by evaporation and the residue is purified by column chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (1:1) as the eluent. Yield: 23.1g (87%). Mp 79-81° C.

Aufarbeitung

  1. temperatureThe mixture is refluxed for 2.5 hours
  2. temperatureAfter cooling the solvent
  3. customis removed by evaporation
  4. customthe residue is purified by column chromatography on silica gel using
  5. additiona mixture of ethyl acetate and petroleum ether (1:1) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-0961fcfc81a14fcfaf9cb8e1dcf8de2d
Quelldatensatz
uspto-grants-1999_05
Patentnummer
US05902813

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