Ethyl Acetate → HCID 178510661, compound
Reaction equation
[C:1]([C:3]1[NH:7][C:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=2[Cl:19])=[N:5][CH:4]=1)#[N:2].[Br:20]Br.C(OCC)(=O)C>ClC(Cl)C(Cl)Cl>[Br:20][C:4]1[N:5]=[C:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([C:15]([F:17])([F:16])[F:18])=[CH:10][C:9]=2[Cl:19])[NH:7][C:3]=1[C:1]#[N:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 5-cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)imidazole (1.0 g, 0.0033 mol) and bromine (1.9 g, 0.64 ml, 0.13 mol) in 1,1,2,2-tetrachloroethane (20 ml) was stirred and heated at 90° C. for 7 hours. Ethyl acetate (50 ml) was added and the solution was washed with water (50 ml), aqueous sodium metabisulphite solution (50 ml). water (50 ml), dried over anhydrous sodium sulphate and evaporated to dryness. The solid residue was purified by chromatography on silica gel elucing with a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.)(3:10) to give 4-bromo-5-cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)imidazole (2.15 g) as a white solid m.p. 270.5°-272° C.
Workup
- washthe solution was washed with water (50 ml), aqueous sodium metabisulphite solution (50 ml)
- dry with materialwater (50 ml), dried over anhydrous sodium sulphate
- customevaporated to dryness
- customThe solid residue was purified by chromatography on silica gel elucing with a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.)(3:10)
Sources & evidence
- ORD record
- ord-f870be53a61e4e6b9d8d27c3157d416c
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05380865
Reaction notes
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