Potassium Carbonate → 2-Bromo-4-(4-chlorophenylthio)-1-(3,3-dichloro-2-propenyloxy)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:16].C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]([Cl:28])=[CH:25][CH2:26]Cl>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:16][CH2:26][CH:25]=[C:24]([Cl:28])[Cl:23]Participants
Procedure
To a mixture of 0.59 g of 2-bromo-4-(4-chlorophenylthio)phenol, 0.28 g of potassium carbonate and 20 ml of N,N-dimethylformamide, a solution prepared by dissolving 0.30 g of 1,1,3-trichloropropene in 5 ml of N,N-dimethylformamide was added dropwise at room temperature with stirring. After the mixture was stirred at room temperature for 6 hours, the reaction solution was poured into ice-water, and extracted twice with 50 ml of diethyl ether. Then, the ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. This crude product was subjected to silica gel column chromatography to give 0.62 g of 2-bromo-4-(4-chlorophenylthio)-1-(3,3-dichloro-2-propenyloxy)benzene, yield 78%; nD25.0 1.6514.
Workup
- customa solution prepared
- additionwas added dropwise at room temperature
- stirringAfter the mixture was stirred at room temperature for 6 hours
- extractionextracted twice with 50 ml of diethyl ether
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customto give a crude product
Sources & evidence
- ORD record
- ord-2761813bcd9246d6bc125292624356c3
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05698702
Reaction notes
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