Methyl iodide → N-BOC-N-Methyl-3-bromoaniline

HRID 1092274

Reaktionsgleichung

Reaktionsgleichung von HRID 1092274
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:18]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:18])[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2757254N-(tert-Butoxycarbonyl)-3-bromoaniline

Produkt 1

HCID 22997148N-BOC-N-Methyl-3-bromoanilineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 114 g (447 mmol) of tert-butyl (3-bromophenyl)carbamate in 800 ml of DMF are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-water and extracted with ethyl acetate. The organic phase is separated out by settling of the phases, dried over magnesium sulfate and evaporated. 115 g of tert-butyl (3-bromophenyl)-N-methylcarbamate are obtained in a yield of 95%.

Aufarbeitung

  1. stirringstirring
  2. extractionextracted with ethyl acetate
  3. customThe organic phase is separated out
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ba3433e1390b426396c07058c5da4ea4
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129416B2

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