Tetrabutylammonium Fluoride → 5-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-trifluoromethyl-3,4-dihydro-2H-pyrrole

HRID 241520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241520
CS[C:3](=[N:12][CH2:13][Si](C)(C)C)[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([Cl:11])[CH:5]=1.[Cl:18][C:19]1[CH:20]=[C:21]([C:26](=[CH2:31])[C:27]([F:30])([F:29])[F:28])[CH:22]=[C:23]([Cl:25])[CH:24]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]2[CH2:31][C:26]([C:21]3[CH:22]=[C:23]([Cl:25])[CH:24]=[C:19]([Cl:18])[CH:20]=3)([C:27]([F:28])([F:30])[F:29])[CH2:13][N:12]=2)=[CH:5][C:6]=1[Cl:11]

Komponenten

5

Edukt 3

HCID 2724141Tetrabutylammonium FluorideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 668366594-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester

Produkt 1

HCID 866910485-(4-bromo-3-chloro-phenyl)-3-(3,5-dichloro-phenyl)-3-trifluoromethyl-3,4-dihydro-2H-pyrroleAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-3-chloro-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (9.60 g, 27.4 mmol) in dry THF (100 mL) was added 2-(3,5-dichlorophenyl)-1,1,1-trifluoro-2-propene (8.94 g, 33.4 mmol) at −7° C. A solution of tetrabutyl ammoniumfluoride (5.32 mL, 1 M in THF, 5.33 mmol) was added at this temperature and the mixture was allowed to warm to room temperature over night. All volatiles were removed in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (9.50 g, 74%).

Aufarbeitung

  1. customAll volatiles were removed in vacuum
  2. customThe residue was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-594cc84a96eb451ca7cfd48e80ed4957
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653000B2

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