1,2-Dibromoethane → 1-(2-Bromoethoxy)-2,4-dichlorobenzene

HRID 20252

Reaktionsgleichung

Reaktionsgleichung von HRID 20252
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Br:10][CH2:11][CH2:12]Br.[OH-].[Na+]>O>[Br:10][CH2:11][CH2:12][O:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Komponenten

5

Edukt 3

HCID 78391,2-DibromoethaneHCID 84492,4-DichlorophenolHCID 14798Sodium Hydroxide

Produkt 1

HCID 1388811-(2-Bromoethoxy)-2,4-dichlorobenzeneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A mixture of 2,4-dichlorophenol (105 g, 0.64 mol), 1,2-dibromoethane (157 g, 0.84 mol) and water (500 mL) was heated at reflux, during which time a solution of sodium hydroxide (28.0 g, 0.70 mol) in water (125 mL) was added to the mixture over a period of one hour. The solution was allowed to reflux for 10 hours, cooled and the separated organic layer was distilled to give 1-bromo-2-(2,4-dichlorophenoxy)ethane (106 g, yield 62%). 1HNMR (CDCl3) δ 7.37 (d, 1H, J=2.4 Hz), 7.19 (dd, 1H, J1=8.8 J2=2.4 Hz), 6.88 (d, 1H, J=8.8 Hz), 4.31 (t, 3H, J=6.4 Hz), 3.65 (t, 3H, J=6.4 Hz).

Aufarbeitung

  1. temperaturewas heated
  2. additionwas added to the mixture over a period of one hour
  3. temperatureto reflux for 10 hours
  4. temperaturecooled
  5. distillationthe separated organic layer was distilled

Quellen und Nachweise

ORD-Eintrag
ord-4af642cd877e42d0a2406a3765dfc027
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745629B2

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