Chlorosuccinimide → 5-Chloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 29378
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[Cl:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([Cl:17])=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 748649Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate

Produkt 1

HCID 687146975-Chloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl esterAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (0.5 g, 2.27 mmol) was added 5 mL of carbon tetrachloride, and the mixture was cooled with an ethanol/ice bath while 1 equivalent of N-chlorosuccinimide was added in small poroom temperatureions. After stirring at −10° C. for 3 h, the reaction mixture was filtered and the filtrate was loaded onto a silica column and chromatographed to give 259 mg (48% yield) of 5-chloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester as an off-white solid.

Aufarbeitung

  1. additionwas added in small poroom temperatureions
  2. filtrationthe reaction mixture was filtered
  3. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-0fc63d910416411a986d0923812e180b
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420001B2

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