Carbon tetrabromide → 4-(2-Chlorobenzyloxy)-3,5-dichloro-1-(3,3-dibromo-2-propenyloxy)benzene
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)[Br:21].[Cl:25][C:26]1[CH:45]=[CH:44][CH:43]=[CH:42][C:27]=1[CH2:28][O:29][C:30]1[C:39]([Cl:40])=[CH:38][C:33]([O:34][CH2:35][CH:36]=O)=[CH:32][C:31]=1[Cl:41]>C(Cl)Cl.[Zn]>[Cl:25][C:26]1[CH:45]=[CH:44][CH:43]=[CH:42][C:27]=1[CH2:28][O:29][C:30]1[C:39]([Cl:40])=[CH:38][C:33]([O:34][CH2:35][CH:36]=[C:20]([Br:24])[Br:21])=[CH:32][C:31]=1[Cl:41]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
In a reaction vessel were placed 0.26 g of zinc dust, 1.0 g of triphenylphosphine, 1.3 g of carbon tetrabromide and 20 ml of methylene chloride, followed by stirring at room temperature. After 24 hours, a solution of 0.70 g of (4-(2-chlorobenzyloxy)-3,5-dichlorophenoxy)acetaldehyde dissolved in 5 ml of methylene chloride was added dropwise to the above solution, while stirring at room temperature. After stirring at room temperature for 6 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.63 g of 4-(2-chlorobenzyloxy)-3,5-dichloro-1-(3,3-dibromo-2-propenyloxy)benzene (63% yield), m.p. 83.5° C.
Workup
- customIn a reaction vessel were placed
- additionwas added dropwise to the above solution
- stirringwhile stirring at room temperature
- stirringAfter stirring at room temperature for 6 hours
- concentrationthe reaction mixture was concentrated
- customto obtain a residue
Sources & evidence
- ORD record
- ord-c70f7546d71c41c5a106ae12f0a82b92
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05872137
Reaction notes
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