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

HRID 1592969Notes

Reaction equation

HRID 1592969 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[H-].[Na+].[CH3:19]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][N:6]([CH3:19])[C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

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

Product 1

HCID 20738487tert-Butyl 3-bromobenzyl(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

128 g (447 mmol) of tert-butyl (3-bromobenzyl)carbamate and 800 ml of DMF are introduced into a round-bottomed flask and under a nitrogen stream. 19 g (475 mmol) of sodium hydride (60% in oil) are added in small quantities and the mixture is stirred until the gas emission ceases. 29.3 ml (470 mmol) of methyl iodide are then added and the mixture is stirred overnight. The reaction medium is poured into ice-cold water, extracted with ethyl acetate, the organic phase decanted off, dried over magnesium sulphate and evaporated off. 152.5 g (92%) of the expected product are recovered.

Workup

  1. stirringthe mixture is stirred overnight
  2. additionThe reaction medium is poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. customthe organic phase decanted off
  5. dry with materialdried over magnesium sulphate
  6. customevaporated off
  7. custom152.5 g (92%) of the expected product are recovered

Sources & evidence

ORD record
ord-3397b448857f49ebaf9dbdecc2995024
Source dataset
uspto-grants-2007_11
Patent number
US07294639B2

Reaction notes

Loading…