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

HRID 1894811Notes

Reaction equation

HRID 1894811 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%.

Workup

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

Sources & evidence

ORD record
ord-b57759fb0ec74548b09c8e913c92bd52
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

Loading…