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

HRID 2247412Notes

Reaction equation

HRID 2247412 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

t-Butyl N-(2-methoxybenzyl)carbamate (6.04 g) was dissolved in 50 ml of acetonitrile, and 4.6 g of N-bromosuccinimide was added thereto. The mixture was stirred at room temperature for 3 hours, and then the solvent was evaporated. The residue was dissolved in ethyl acetate and successively washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was washed with a mixed solvent of t-butyl methyl 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. washsuccessively washed with water and 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 solvent of t-butyl methyl ether and hexane

Sources & evidence

ORD record
ord-647d908904764a3f99f61637e9cb43fb
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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