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

HRID 1296216

Reaction equation

HRID 1296216 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 for 3 hours at room temperature, the solvent was evaporated. The residue was dissolved in ethyl acetate, and successively washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was washed with mixture solution of methyl t-butylmethyl ether and hexane, to give 6.97 g of t-butyl N-(5-bromo-2-methoxybenzyl)carbamate.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washsuccessively washed 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 mixture solution of methyl t-butylmethyl ether and hexane

Sources & evidence

ORD record
ord-52512523871d4e4d8e460cff3db66c96
Source dataset
uspto-grants-2007_07
Patent number
US07244861B2

Linked notes

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