Tetrahydrofuran → 2-Bromo-9,9-dimethoxyethylfluorene

HRID 720019

Reaktionsgleichung

Reaktionsgleichung von HRID 720019
[Br:1][C:2]1C=[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.[CH3:15][C:16]([CH3:19])([O-:18])C.[K+].S([O:25][CH2:26]COC)(=O)(=O)C.O1CCC[CH2:31]1>O>[Br:1][CH2:2][CH2:3][C:4]1[C:15]2[C:16]([O:25][CH3:26])([O:18][CH3:31])[C:19]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 143362-Bromo-9H-fluoreneHCID 1462932-Methoxyethyl methanesulfonateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 695870882-Bromo-9,9-dimethoxyethylfluorene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2-bromofluorene (2.45 g, 10 mmol) in tetrahydrofuran (dry, 75 ml) was added potassium t-butoxide (3.36 g, 30 mmol), giving a deep orange solution. The mixture was stirred at ambient temperature for 10 min and added 2-methoxyethyl mesylate in tetrahydrofuran dropwise. Exothermic reaction was observed. Stirring was continued at ambient temperature for overnight to give an orange solution. At the end of the reaction, it was diluted with water (150 ml). The products extracted with ethylacetate (30 ml) and washed with water. Organic layer was dried over magnesium sulfate and concentrated in vacuuo to afford the crude product. It was purified by preparative thin layer chromatography (silica gel, Rf=0.3 using hexane-EtOAc/3:2 as eluent) to give 2-bromo-9,9-dimethoxyethylfluorene (3.3 g).

Aufarbeitung

  1. customgiving a deep orange solution
  2. customExothermic reaction
  3. stirringStirring
  4. waitwas continued at ambient temperature for overnight
  5. customto give an orange solution
  6. customAt the end of the reaction, it
  7. extractionThe products extracted with ethylacetate (30 ml)
  8. washwashed with water
  9. dry with materialOrganic layer was dried over magnesium sulfate
  10. concentrationconcentrated in vacuuo
  11. customto afford the crude product
  12. customIt was purified by preparative thin layer chromatography (silica gel, Rf=0.3 using hexane-EtOAc/3:2 as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-67040ca6b49542a6ac6a7c0f8ef870c1
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132572B2

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