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

HRID 250818

Reaktionsgleichung

Reaktionsgleichung von HRID 250818
[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-cold water and extracted with ethyl acetate. The organic phase is separated out after 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. additionThe reaction medium is poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. customThe organic phase is separated out
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9e174b4906214e0bad73be36a5c81fc0
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863332B2

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