Methyl iodide → tert-Butyl (4-bromophenyl)methylcarbamate

HRID 1867516Notes

Reaction equation

HRID 1867516 reaction equation
IC.[C:3]([O:7][C:8](=[O:17])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)([CH3:6])([CH3:5])[CH3:4].[C:18](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:3]([O:7][C:8](=[O:17])[N:9]([C:10]1[CH:11]=[CH:12][C:13]([Br:16])=[CH:14][CH:15]=1)[CH3:18])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 27736084-Bromoaniline, N-BOC protected

Product 1

HCID 21873211tert-Butyl (4-bromophenyl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.263 mL (1.1 eq.) iodomethane are added dropwise at room temperature to a stirred suspension of 1.1 g (4 mmol) (4-bromo-phenyl)-carbamic acid tert-butyl ester and 2 g (1.6 eq.) cesium carbonate in 15 mL DMF. After stirring for an additional 18 hours, the reaction mixture is extracted with water/ethyl acetate and the combined organic phases are washed with brine, dried over magnesium sulfate and evaporated to yield the desired product as a colorless oil, which is used without further purification.

Workup

  1. extractionthe reaction mixture is extracted with water/ethyl acetate
  2. washthe combined organic phases are washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-3141bbca147b4d31be01ec0250486f34
Source dataset
uspto-grants-2009_12
Patent number
US07632851B2

Reaction notes

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