Dimethyl Sulfoxide → HCID 21885620, Verbindung

HRID 1358060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358060
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.CS(C)=O.[OH-].[Na+].[CH2:22]([CH:24]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:25]Br)[CH3:23]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)C.O>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=3)[C:5]([CH2:5][CH:4]([CH2:12][CH3:11])[CH2:3][CH2:2][CH2:14][CH3:13])([CH2:25][CH:24]([CH2:22][CH3:23])[CH2:27][CH2:28][CH2:29][CH3:30])[C:4]=2[CH:3]=1

Komponenten

8

Edukt 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 868042-Ethylhexyl bromide2×HCID 2519872,7-Dichlorofluorene2×

Produkt 1

HCID 21885620HCID 21885620, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a stirred mixture of 2,7-dichlorofluorene (43 g, 0.183 mole) and 120 mL of dimethylsulfoxide (DMSO) under nitrogen was added benzyltriethylammonium chloride (2.3 g, 0.01 mole) and 60 mL of a 50 weight percent aqueous solution of sodium hydroxide. 2-Ethylhexyl bromide (85 g, 0.44 mole) was added and the mixture was agitated well for 2 hours. The reaction was exothermic, the temperature reaching 80° C. within 5 minutes after the addition of 2-ethylhexyl bromide and then falling off to 30° C. over the 2-hour reaction time. Analysis of an aliquot by high pressure liquid chromatography (HPLC) showed the complete disappearance of 2,7-dichlorofluorene and the formation of new product. Water (200 mL), and diethyl ether (250 mL) were added to the reaction mixture, stirred for 15 minutes and the layers were separated. The organic layer was washed with a saturated aqueous NaCl solution, water, dried (MgSO4) and evaporated to remove ether. Fractional vacuum distillation of the residue provided 2,7-dichloro-9,9-di(2-ethylhexyl)fluorene as clear liquid, boiling point 200° C./1 mm Hg, (79 g, 94 percent yield); HPLC analysis showed that the product was 99 percent pure; Proton Magnetic Spectrum (PMR) analysis was consistent with the title structure.

Aufarbeitung

  1. waitthe temperature reaching 80° C. within 5 minutes
  2. customfalling off to 30° C. over the 2-hour reaction time
  3. stirringstirred for 15 minutes
  4. customthe layers were separated
  5. washThe organic layer was washed with a saturated aqueous NaCl solution, water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto remove ether
  9. distillationFractional vacuum distillation of the residue

Quellen und Nachweise

ORD-Eintrag
ord-66fc72881db54737a07af2d2fae763b6
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593450B2

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