N-Iodosuccinimide → Methyl 4-bromo-2-iodophenylcarbamate

HRID 397314Notes

Reaction equation

HRID 397314 reaction equation
[I:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11](=[O:20])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1>C(#N)C>[CH3:9][O:10][C:11](=[O:20])[NH:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[I:1]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 5203164methyl N-(4-bromophenyl)carbamate

Product 1

HCID 23643163Methyl 4-bromo-2-iodophenylcarbamateYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

133 g (0.591 mol) N-iodosuccinimide and 5.0 mL (8.60 g, 0.0573 mol) trifuoromethanesulfonic acid were added to a solution of 130.0 g (0.5651 mol) of (4-bromo-phenyl)-carbamic acid methyl ester in 660 mL acetonitrile. The mixture was stirred at room temperature for 18 h. The precipitate was collected by filtration washed with 160 mL ice-cold acetonitrile and dried to constant weight to yield 187.0 g (92%) of the title compound as white crystals melting at 129.4-130.0° C.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with 160 mL ice-cold acetonitrile
  3. customdried to constant weight

Sources & evidence

ORD record
ord-16655706fa124233a0f5698b7dc295b6
Source dataset
uspto-grants-2003_08
Patent number
US06610685B2

Reaction notes

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