N-Iodosuccinimide → HCID 57481199, compound

HRID 1183200Notes

Reaction equation

HRID 1183200 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH3:13])[CH:12]=2)=[CH:4][CH:3]=1.[I:14]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>ClCCl.FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH3:13])[C:12]=2[I:14])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 532492914-(4-Bromophenyl)-1-methyl-1H-imidazole

Product 1

HCID 57481199HCID 57481199, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-bromophenyl)-1-methyl-1H-imidazole (Step 2 product, 2.8 g, 9.45 mmol) in dichloromethane (30 mL) was added N-iodosuccinimide (1.913 g, 8.50 mmol) and six drops of trifluoroacetic acid. The reaction mixture was stirred at rt for 16 h. The mixture was neutralized with aqueous sodium bicarbonate and the organics were extracted with dichloromethane. The organics were then washed with aqueous sodium thiosulfate, followed by three washes with water then dried (MgSO4). The solvent was concentrated to afford 4-(4-bromophenyl)-5-iodo-1-methyl-1H-imidazole, which was used with out further purification. LCMS: [M+1]+=363.

Workup

  1. extractionthe organics were extracted with dichloromethane
  2. washThe organics were then washed with aqueous sodium thiosulfate
  3. dry with materialthen dried (MgSO4)
  4. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-20a6eb2f96674e79a856d8ffd33cd766
Source dataset
uspto-grants-2014_03
Patent number
US08664253B2

Reaction notes

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