Sodium Carbonate → HCID 59229504, Verbindung

HRID 1640097

Reaktionsgleichung

Reaktionsgleichung von HRID 1640097
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Cl.[F:13][C:14]([F:29])([F:28])[C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.COCCOC.C(OCC)(=O)C>[F:13][C:14]([F:28])([F:29])[C:15]1[CH:16]=[C:17]([CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=1)[CH2:5][C:4]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 87687Alpha-chloro-3-methyl-4-nitrotolueneHCID 1562653,5-Bis-trifluoromethylphenylboronic acid

Produkt 1

HCID 59229504HCID 59229504, VerbindungAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-methyl-4-nitrobenzyl chloride (0.27 g), 3,5-bis-(trifluoromethyl)phenylboronic acid (0.45 g), tetrakis(triphenylphosfine)palladium (0.1 g) and sodium carbonate (0.48 g) in water (2 ml) and 1,2-dimethoxyethane (10 ml) was stirred under an argon atmosphere at 85° C. for 2 hours. After cooling, the reaction solution was diluted with ethyl acetate and further stirred for 10 minutes by adding water thereto. After washing the organic layer with a saturated salt solution, it was dried over anhydrous magnesium sulfate. The solution was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography to obtain 4-(3,5-bis-trifluoromethyl-benzyl)-2-methyl-nitrobenzene (0.44 g).

Aufarbeitung

  1. temperatureAfter cooling
  2. washAfter washing the organic layer with a saturated salt solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationThe solution was distilled off under reduced pressure
  5. customthe resultant residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8c6e98deb47f4c6d8b0369cd3fdafd97
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110689B2

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