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

HRID 1009216Notes

Reaction equation

HRID 1009216 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)C=O>[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 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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

Workup

  1. stirringstirring
  2. temperatureis maintained for 18 hours
  3. additionThe reaction medium is poured into ice-cold water
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-a615e16705fe45c9894a772cb6d86369
Source dataset
uspto-grants-2011_07
Patent number
US07973063B2

Reaction notes

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