N-Iodosuccinimide → HCID 50999508, compound

HRID 588802Notes

Reaction equation

HRID 588802 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[Cl:8].C1C(=O)N([I:17])C(=O)C1>CC(O)=O>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([I:17])=[C:4]([NH2:9])[CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 128437223-Bromo-4-chloroaniline

Product 1

HCID 50999508HCID 50999508, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-bromo-4-chlorobenzenamine (10.0 g, 48.5 mmol) in CH3COOH (50 mL), NIS (10.9 g, 48.5 mmol) was added in portions and the resulting mixture was stirred at room temperature for 16 h. The mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=50:1) to afford the desired product (2.5 g, 15.5% yield). ESI-MS m/z: 329.9 [M−H]−.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=50:1)

Sources & evidence

ORD record
ord-959f52af961e4af7bb29aa1f1d0e7f23
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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