Ethyl bromoacetate → Ethyl 2-(2-acetyl-4-bromophenoxy)acetate

HRID 29295

Reaktionsgleichung

Reaktionsgleichung von HRID 29295
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18]([O:20][C:21](=[O:24])[CH2:22]Br)[CH3:19]>CN(C=O)C>[CH2:18]([O:20][C:21](=[O:24])[CH2:22][O:11][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[C:8](=[O:10])[CH3:9])[CH3:19]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 959915'-Bromo-2'-hydroxyacetophenone

Produkt 1

HCID 19261366Ethyl 2-(2-acetyl-4-bromophenoxy)acetateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (2.1 g, 9.8 mmol, 1 eq) and K2CO3 (2.4 g, 17.4 mmol, 1.8 eq) in 15 mL of DMF was added 1.3 mL of bromo-acetic acid ethyl ester (11.7 mmol, 1.2 eq) under nitrogen. After 12 h, the mixture was worked up and crude compound recrystallized to give (2-acetyl-4-bromo-phenoxy)-acetic acid ethyl ester in 97% yield (2.87 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.3 (t, J=7.1 Hz, 3 H) 2.7 (s, 3 H) 4.3 (q, J=7.1 Hz, 2 H) 4.7 (s, 2 H) 6.7 (d, J=8.8 Hz, 1 H) 7.5 (dd, J=8.8, 2.8 Hz, 1 H) 7.9 (d, J=2.8 Hz, 1 H).

Aufarbeitung

  1. customcrude compound recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-74d24ce1bc884b41a7d0e97b51d9a336
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420001B2

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