N-bromobutanimide → bis(4-Fluorophenyl)methyl(5-bromo-1H-1,2,4-triazol-1-ylmethyl)silane

HRID 568778

Reaktionsgleichung

Reaktionsgleichung von HRID 568778
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH3:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([Si:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([CH3:15])[CH2:9][N:10]2[C:14]([Br:23])=[N:13][CH:12]=[N:11]2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 73675Flusilazole

Produkt 1

HCID 53907273bis(4-Fluorophenyl)methyl(5-bromo-1H-1,2,4-triazol-1-ylmethyl)silaneAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 1.5 g (0.0050 mol) of bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-ylmethyl)silane, 0.98 g (0.0055 mol) of N-bromosuccinimide and ~1 mg of azobisisobutyltronitrile in 10 mL of CCl4 was warmed to 60°, then illuminated with a high intensity lamp (Roxter Model 5900) for 20 minutes. The mixture was cooled, filtered, and evaporated, and the residue was flash chromatographed (10% ether/methylene chloride) to give 1.7 g of the title compound as an oil: ir (neat) 3030, 2960, 1590, 1498, 1479, 1339, 1265, 1231, 1162, 1108, 1033, 825, 789, 733 cm-1. nmr (CDCl3) δ0.7 (s, 9H), 4.2 (s, 2H, 7.1 (t, 4H), 7.5 (m, 4H), 7.8 (s, 1H).

Aufarbeitung

  1. temperaturewas warmed to 60°
  2. customilluminated with a high intensity lamp (Roxter Model 5900) for 20 minutes
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customevaporated
  6. customchromatographed (10% ether/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-e6b7356ce3814576b6adc3f24b98ca98
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04729986

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