Water → HCID 178506192, compound

HRID 1769284Notes

Reaction equation

HRID 1769284 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]1[NH:14][CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:17]=1.[Br:22]Br.O>C(O)(=O)C>[Br:22][C:15]1[NH:14][C:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:10])([F:9])[F:11])=[CH:5][C:4]=2[Cl:12])=[N:17][C:16]=1[C:18]([F:21])([F:19])[F:20]

Participants

5

Reactant 3

HCID 962Water2×HCID 24408Bromine2×HCID 178506193HCID 178506193, compound

Product 1

HCID 178506192HCID 178506192, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylimidazole (0.7 g, 0.002 mol) and bromine (0.32 g, 0.1 ml, 0.002 mol) in glacial acetic acid (5 ml) was stirred and heated at reflux for 2 hours. The cooled suspension was poured into cold water (50 ml) and the solid was filtered and washed with water. The solid was dissolved in glacial acetic acid (5 ml) and bromine (0.32 g, 0.1 ml, 0.002 mol) was added. The mixture was stirred and heated at reflux for 2 hours, cooled and poured into cold water (50 ml). The solid was filtered and washed thoroughly with water to give 5-bromo-2-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylimidazole (0.6 g) as a white solid, m.p. 295° C. with decomposition.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. filtrationthe solid was filtered
  4. washwashed with water
  5. dissolutionThe solid was dissolved in glacial acetic acid (5 ml)
  6. temperatureheated
  7. temperatureat reflux for 2 hours
  8. temperaturecooled
  9. filtrationThe solid was filtered
  10. washwashed thoroughly with water

Sources & evidence

ORD record
ord-1b0e30b8ae1b4e6583de828e2f32f602
Source dataset
uspto-grants-1995_01
Patent number
US05380865

Reaction notes

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