Toluene → HCID 86677616, compound
Reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:10]=[C:11]([CH:16](Br)[C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][C:14]=1[Cl:15].[C:22]([O-])(=[S:24])[CH3:23].[K+]>CO>[C:22]([CH:16]([C:11]1[CH:12]=[CH:13][C:14]([Cl:15])=[C:9]([Cl:8])[CH:10]=1)[C:17]([O:19][CH3:20])=[O:18])(=[S:24])[CH3:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A toluene (403 mL) solution of methyl 2-(3,4-dichlorophenyl)-2-bromoacetate (134 g, 0.451 mol) was dropwise added to a methanol (403 mL) solution of potassium thioacetate (67.7 g, 0.586 mol, 1.3 equivalent amounts based on the starting material) at 5° C. over a period of 15 minutes, followed by stirring at 5° C. for 1 hour. The formed solid was subjected to filtration, and the filtrate was mixed with toluene (403 mL), sequentially washed with water, a saturated sodium hydrogencarbonate aqueous solution, a saturated ammonium chloride aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off to give the desired product as a yellow oil (136 g, yield: 103%).
Workup
- customat 5° C.
- customof 15 minutes
- filtrationThe formed solid was subjected to filtration
- additionthe filtrate was mixed with toluene (403 mL)
- washsequentially washed with water
- dry with materiala saturated sodium hydrogencarbonate aqueous solution, a saturated ammonium chloride aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate
- customThe drying agent was removed by filtration
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-73b2ce92ff444127b0c6ead87949b123
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642786B2
Reaction notes
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