Dimethyl Sulfoxide → HCID 21885620, Verbindung

HRID 1383707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383707
[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, Verbindung

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 is 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) is added and the mixture is agitated well for 2 hours. The reaction is 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) shows the complete disappearance of 2,7-dichlorofluorene and the formation of new product. Water (200 mL), and diethyl ether (250 mL) are added to the reaction mixture, stirred for 15 minutes and the layers are separated. The organic layer is washed with a saturated aqueous NaCl solution, water, dried (MgSO4) and evaporated to remove ether. Fractional vacuum distillation of the residue provides 2,7-dichloro-9,9-di(2-ethylhexyl)-fluorene as clear liquid, boiling point 200° C./l mm Hg, (79 g, 94 percent yield); HPLC analysis shows that the product is 99 percent pure. Proton Magnetic Spectrum (PMR) analysis is 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 are separated
  5. washThe organic layer is 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-c67516014a0c48b58073e1108d42f6cc
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255449B1

Notizen zur Reaktion

Wird geladen…