N-bromobutanimide → Tert-butyl (5-bromo-2-methoxybenzyl)carbamate

HRID 1985293Notes

Reaction equation

HRID 1985293 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[Br:18]N1C(=O)CCC1=O>C(#N)C>[Br:18][C:15]1[CH:16]=[CH:17][C:3]([O:2][CH3:1])=[C:4]([CH:14]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22926021Tert-butyl (2-methoxybenzyl)carbamate

Product 1

HCID 22926030Tert-butyl (5-bromo-2-methoxybenzyl)carbamateYield 86.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.04 g of t-Butyl N-(2-methoxybenzyl)carbamate was dissolved in 50 ml of acetonitrile, and 4.6 g of N-bromosuccinimide was added. After stirring was continued at room temperature for 3 hours, the solvent was evaporated. The residue was dissolved in ethyl acetate, and washed successively with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was washed with a mixed solution of methyl t-butyl ether and hexane, to give 6.97 g of the title compound.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed successively with water and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. washThe residue was washed with a mixed solution of methyl t-butyl ether and hexane

Sources & evidence

ORD record
ord-7df243ff2a4f4008a919224b26af209b
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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