Methyl iodide → tert-Butyl 3-bromobenzyl(methyl)carbamate

HRID 1181652Notes

Reaction equation

HRID 1181652 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[CH3:19]I>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7][N:8]([CH3:19])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11033439tert-Butyl 3-bromobenzylcarbamate

Product 1

HCID 20738487tert-Butyl 3-bromobenzyl(methyl)carbamateYield 113.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19 g (475 mmol) of sodium hydride (60% in oil) are added portionwise to a solution of 128 g (447 mmol) of tert-butyl (3-bromobenzyl)carbamate in 800 ml of DMF, 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 by settling of the phases, dried over magnesium sulfate and evaporated. 152.5 g of tert-butyl (3-bromobenzyl)-N-methylcarbamate are obtained in a yield of 92%.

Workup

  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

Sources & evidence

ORD record
ord-d20194bb04e44a5984fbdec8e481e0b2
Source dataset
uspto-grants-2007_10
Patent number
US07285568B2

Reaction notes

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