o-Iodoanisole → Methyl 3,5-dibromo-4-(3-iodo-4-methoxyphenylthio)phenylacetate

HRID 1975265

Reaktionsgleichung

Reaktionsgleichung von HRID 1975265
C(C1C=CC=CC=1OC)(C)C.[Br:12][C:13]1[CH:14]=[C:15]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:16]=[C:17]([Br:20])[C:18]=1[SH:19].[I:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH3:34]>>[Br:12][C:13]1[CH:14]=[C:15]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:16]=[C:17]([Br:20])[C:18]=1[S:19][C:31]1[CH:30]=[CH:29][C:28]([O:33][CH3:34])=[C:27]([I:26])[CH:32]=1

Komponenten

4

Edukt 3

HCID 68257o-IodoanisoleHCID 2706232-IsopropylanisoleHCID 19101399Methyl 3,5-dibromo-4-mercaptophenylacetate

Produkt 1

HCID 19101415Methyl 3,5-dibromo-4-(3-iodo-4-methoxyphenylthio)phenylacetateAusbeute 83,2 %

Versuchsvorschrift

Following the procedures of Example 1, but substituting 2-iodoanisole for 2-isopropylanisole, methyl 3,5-dibromo-4-mercaptophenylacetate (1 g) was reacted with 2-iodoanisole (0.7 g) to yield the thioether, methyl 3,5-dibromo-4-(3-iodo-4-methoxyphenylthio)phenylacetate (1.4 g) which in turn was oxidized to methyl 3,5-dibromo-4-(3-iodo-4-methoxyphenylsulfonyl)phenylacetate, MP: 127°-129° C. The acetate was saponified to the acid, 3,5-dibromo-4-(3-iodo-4-methoxyphenylsulfonyl)phenylacetic acid, MP: 158°-162° C.

Quellen und Nachweise

ORD-Eintrag
ord-26ec20d2137d47b8a8041176bf5a81d9
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05284971

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