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Dimethyl Sulfoxide → 2-Bromo-9,9-di-n-octylfluorene

HRID 11181
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 11181
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.CS(C)=O.[OH-].[Na+].[CH2:21](Br)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CCCCCC.O.CCOCC>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:13][CH2:14][CH2:2][CH2:3][CH2:4][CH2:12][CH2:11][CH3:10])([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:4]=2[CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 679Dimethyl SulfoxideHCID 81401-BromooctaneHCID 143362-Bromo-9H-fluoreneHCID 14798Sodium Hydroxide

Produkt 1

HCID 129646932-Bromo-9,9-di-n-octylfluoreneAusbeute 155,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133
Benzyl triethylammonium chloride
Katalysator
HCID 8058HexaneLösungsmittel
HCID 21584184Diethylether waterLösungsmittel

Versuchsvorschrift

A 3L flask fitted with a mechanical stirrer was charged with 2-bromofluorene (45 g, 183.6 mmole) and 150 mL DMSO. Under a N2 atmosphere was added 80 mL of a 50% aqueous NaOH solution and 2.72 g of benzyltriethylammonium chloride (2.72 g, 11.98 mmole). This was stirred for 2 h at RT. With vigorous mechanical stirring, n-octylbromide (84.96 g, 440 mmole) was added via a dropping funnel (exotherm). Stirring was continued for 2 hours. To the reaction mixture was added 500 mL of a 1:1 mixture of water/ether, and the organic layer separated and was washed successively with brine and then water. Drying over magnesium sulfate and evaporation of the solvent gave an oil. Purification by column chromatography (silica gel; hexane as the mobile phase) gave 67 g (78% yield) of 2-bromo-9,9-dioctylfluorene as a pale oil.

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for 2 hours
  3. additionTo the reaction mixture was added
  4. customthe organic layer separated
  5. washwas washed successively with brine
  6. dry with materialDrying over magnesium sulfate and evaporation of the solvent
  7. customgave an oil
  8. customPurification by column chromatography (silica gel

Quellen und Nachweise

ORD-Eintrag
ord-07d99d444aa441219797fc1437284320
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07094902B2

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