Methyl 4-chloro-3-nitrobenzoate → Methyl 4-(methylsulfanyl)-3-nitrobenzenecarboxylate

HRID 356917

Reaktionsgleichung

Reaktionsgleichung von HRID 356917
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][S-:16].[Na+]>CC(C)=O>[CH3:15][S:16][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Komponenten

4

Edukt 2

HCID 735797Methyl 4-chloro-3-nitrobenzoateHCID 4378561Sodium methanethiolate

Produkt 1

HCID 21187831Methyl 4-(methylsulfanyl)-3-nitrobenzenecarboxylateAusbeute 62,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A solution of methyl 4-chloro-3-nitrobenzoate (28 g) in acetone (250 mL) is treated portionwise with sodium thiomethoxide (10 g) and the mixture is stirred overnight at room temperature. After filtration, the solution is concentrated and water (300 mL) is added to the residue. The yellow solid is filtered off and subjected to flash chromatography eluting with a mixture of diethyl ether and pentane (1:4 v/v), to give methyl 4-methylthio-3-nitrobenzoate (18.5 g), in the form of a yellow solid, m.p. 118°-120° C.

Aufarbeitung

  1. filtrationAfter filtration
  2. concentrationthe solution is concentrated
  3. additionwater (300 mL) is added to the residue
  4. filtrationThe yellow solid is filtered off
  5. washeluting with a mixture of diethyl ether and pentane (1:4 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-ee20706d8f2f4788a12ee24e21de5d84
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840724

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