Trifluoromethanesulfonic acid → Methyl (4-Bromo-2-iodo-5-methylphenyl)carbamate

HRID 853095Notes

Reaction equation

HRID 853095 reaction equation
[CH3:1][O:2][C:3](=[O:13])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[CH:6]=1.[I:14]N1C(=O)CCC1=O.FC(F)(F)S(O)(=O)=O>C(#N)C>[CH3:1][O:2][C:3](=[O:13])[NH:4][C:5]1[CH:6]=[C:7]([CH3:12])[C:8]([Br:11])=[CH:9][C:10]=1[I:14]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 28378453Methyl (4-bromo-3-methylphenyl)carbamate

Product 1

HCID 57543475Methyl (4-Bromo-2-iodo-5-methylphenyl)carbamateYield 76.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5.00 g (4-bromo-3-methyl-phenyl)-carbamic acid methyl ester in 50 ml acetonitrile were added at 0° C. 4.84 g N-iodosuccinimide and 0.18-ml trifluoromethanesulfonic acid. The mixture was stirred 18 h at room temperature. The solid was collected by filtration, washed with cold acetonitrile and dried to constant weight to yield 5.80 g (4-bromo-2-iodo-5-methyl-phenyl)-carbamic acid methyl ester as white crystals melting at 140–141° C.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with cold acetonitrile
  3. customdried to constant weight

Sources & evidence

ORD record
ord-d66bd5b40a1e4ea09c87fff2a0c29c38
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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