Sodium Carbonate → HCID 178444527, Verbindung

HRID 841846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 841846
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].OB(O)[C:23]1[CH:28]=[C:27]([F:29])[C:26]([O:30][C:31]([F:34])([F:33])[F:32])=[C:25]([F:35])[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].O>[F:29][C:27]1[CH:28]=[C:23]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][C@H:9]3[CH2:10][CH2:11][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]3)=[CH:15][CH:16]=2)[CH:24]=[C:25]([F:35])[C:26]=1[O:30][C:31]([F:32])([F:33])[F:34]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 23443787B-[3,5-Difluoro-4-(trifluoromethoxy)phenyl]boronic acidHCID 178444532HCID 178444532, Verbindung

Produkt 1

HCID 178444527HCID 178444527, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5.0 g (13 mmol) of 4-(trans-4-pentylcyclohexyl) methoxyiodo benzene, 4.1 g (34 mmol) of dihydroxy (3,5-difluoro-4-trifluoromethoxyphenyl) borane, 3.0 g of 5% palladium on activated charcoal and 7.2 g (136 mmol) of sodium carbonate was refluxed in toluene/alcohol/water (1/1/1 v/v, 75 ml) under a nitrogen atmosphere for 3 days. After cooling, the reaction solution was added with water (100 ml) and extracted twice with toluene (100 ml). An organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent therein was distilled off under a reduced pressure. The residue thus obtained was purified by column chromatography (silica gel/heptane:toluene=5:1) and recrystallization (heptane-ethanol) to obtain colorless crystals of 2,6-difluoro-4-(4-(trans-4-pentylcyclohexyl) methoxyphenyl) trifluoromethoxybenzene.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted twice with toluene (100 ml)
  3. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent therein was distilled off under a reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography (silica gel/heptane:toluene=5:1) and recrystallization (heptane-ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-d35764cb91854d54a29b0309e10c4a03
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06372153B1

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