Methyl iodide → Methyl 3-bromo-4-(pyrrolidin-1-ylcarbonyl)benzoate

HRID 2053762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053762
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:5]([OH:7])=[O:6].[C:18](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:5]([O:7][CH3:18])=[O:6]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 693124883-Bromo-4-(pyrrolidin-1-ylcarbonyl)benzoic acid

Produkt 1

HCID 69312594Methyl 3-bromo-4-(pyrrolidin-1-ylcarbonyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

20 g (67.1 mmol) of 3-bromo-4-(pyrrolidin-1-ylcarbonyl)benzoic acid is dissolved in 400 mL of N,N-dimethylformamide and combined with 21.9 g (67.1 mmol) cesium carbonate with stirring. Then 4.21 mL (67.1 mmol) of iodomethane is slowly added dropwise at ambient temperature and the mixture is stirred for 16 hours at ambient temperature. After the solid constituents have been removed by filtration with suction, volatile constituents are removed in vacuo. Yield: 20.94 g (75%); Rf value: 0.42 (silica gel; dichloromethane/ethanol=98:2); C13H14BrNO3 (312.17); mass spectrum: (M+H)+=312/314 (bromine isotope).

Aufarbeitung

  1. stirringthe mixture is stirred for 16 hours at ambient temperature
  2. customAfter the solid constituents have been removed by filtration with suction, volatile constituents
  3. customare removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1f631f885c4c4dd887240ea6ca9a1da1
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326791B2

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