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

HRID 1244642Notes

Reaction equation

HRID 1244642 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-bb9b97f4a86b45e2868734090663dc59
Source dataset
uspto-grants-2006_10
Patent number
US07122564B2

Reaction notes

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