Bromine → 4-Bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)pyrrole-3-carbonitrile
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:19])[C:10]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.[Br:20]Br>ClC1C=CC=CC=1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH3:19])[C:10]([C:15]([F:18])([F:16])[F:17])=[C:11]([Br:20])[C:12]=2[C:13]#[N:14])=[CH:6][CH:7]=1Komponenten
6
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A solution of 2-(p-chlorophenyl)-1-methyl-5-(trifluoromethyl)pyrrole-3-carbonitrile (5.70 g, 0.02 mol) in chlorobenzene is treated with bromine (3.52 g, 0.022 mol), heated at 80° C. for 20 hours, cooled to room temperature, treated with additional bromine (3.52 g, 0.022 mol) and heated at 100° C. until reaction is complete by HPLC analysis. The reaction mixture is cooled to room temperature and diluted with ethyl acetate and water. The organic phase is washed with aqueous sodium metabisulfite, dried (MgSO4) and concentrated in vacuo to afford a solid residue. The residue is recrystallized from ethyl acetate/heptane to give the title product as a white solid, 6.50 g (89.4% yield), mp 126°-129° C.
Aufarbeitung
- temperaturecooled to room temperature
- temperatureheated at 100° C. until reaction
- temperatureThe reaction mixture is cooled to room temperature
- washThe organic phase is washed with aqueous sodium metabisulfite
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto afford a solid residue
- customThe residue is recrystallized from ethyl acetate/heptane
Quellen und Nachweise
- ORD-Eintrag
- ord-eecfa46de4a149aabb45ebe0dcb1230c
- Quelldatensatz
- uspto-grants-1992_09
- Patentnummer
- US05144041
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