Iodine → HCID 178432833, compound

HRID 1754369Notes

Reaction equation

HRID 1754369 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.C(Cl)(Cl)Cl.[I:15]I>CC(O)=O>[I:15][C:4]1[NH:3][C:2]([CH3:1])=[N:6][C:5]=1[C:7]([F:10])([F:9])[F:8]

Participants

5

Reactant 3

HCID 807IodineHCID 6212ChloroformHCID 178432834HCID 178432834, compound

Product 1

HCID 178432833HCID 178432833, compoundYield 107.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To 2-methyl-4-(trifluoromethyl)-1H-imidazole (1 g, 6.7 mmol) was added CHCl3 (4.5 mL) and AcOH (13.5 mL) followed by I2 (1.78 g, 6.99 mmol) and HIO4.2H2O (1.52 g, 6.7 mmol), and the resulting reaction mixture was stirred at 60° C. for 3 h. The reaction mixture was then poured into ice cold 10% aqueous sodium bisulphite solution (100 mL) and the aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine (100 mL), dried (MgSO4) and concentrated in vacuo to obtain 5-iodo-2-methyl-4-(trifluoromethyl)-1H-imidazole (1.98 g) which was used as such in next step without further purification.

Workup

  1. customthe resulting reaction mixture
  2. extractionthe aqueous layer was extracted with EtOAc (3×100 mL)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b79a78fc6cc248c9a7bf201f7e8a7dc8
Source dataset
uspto-grants-2015_10
Patent number
US09169248B2

Reaction notes

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