1,2-Dibromoethane → 1-[2-(2-Bromoethoxy)-1-(3-fluorophenyl)ethenyl]-3-fluorobenzene

HRID 1460663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1460663
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[Br:20][CH2:21][CH2:22]Br>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+].O>[Br:20][CH2:21][CH2:22][O:10][CH:9]=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Komponenten

7

Edukt 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 54068354HCID 54068354, Verbindung

Produkt 1

HCID 106884311-[2-(2-Bromoethoxy)-1-(3-fluorophenyl)ethenyl]-3-fluorobenzeneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

bis(3-Fluorophenyl)acetaldehyde (4.82 g, 0.0208 mol) was dissolved in dichloromethane (50 ml) and tetra-n-butyl ammonium bromide (0.67 g, 0.00208 mol) was added. 12N sodium hydroxide solution (50 ml) and 1,2-dibromoethane (17.9 ml, 0.208 mol) Were introduced and the mixture was stirred vigorously at room temperature for 20 h. Dichloromethane (100 ml) and saturated brine (50 ml) were added, and the phases were separated. The aqueous phase was extracted further with dichloromethane (50 ml) and the combined dichloromethane extracts were washed with water (2×75 ml) and saturated brine (50 ml). Drying of the dichloromethane solution (Na2SO4) and evaporation provided the title compound as an oil (6.66 g, 95%), TLC rf 0.71 (SiO2 : dichloromethane).

Aufarbeitung

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted further with dichloromethane (50 ml)
  3. washthe combined dichloromethane extracts were washed with water (2×75 ml) and saturated brine (50 ml)
  4. dry with materialDrying of the dichloromethane solution (Na2SO4) and evaporation

Quellen und Nachweise

ORD-Eintrag
ord-63ffd652700348989622f3c232281845
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05071859

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