2-Chlorophenol → Ethyl (4-chlorosulfonyl-2-chloro-phenoxy)-acetate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[Cl:22][S:23](O)(=[O:25])=[O:24]>CC(=O)CC.ClCCl>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:8][C:3]1[CH:4]=[CH:5][C:6]([S:23]([Cl:22])(=[O:25])=[O:24])=[CH:7][C:2]=1[Cl:1])[CH3:21]Participants
Procedure
A solution of 2-chlorophenol (25.7 g, 200 mmol), potassium carbonate (41.4 g, 300 mmol) and ethyl bromoacetate (35.1 g, 210 mmol) in 2-butanone (240 ml) was stirred at 100° C. for 24 h. The reaction mixture was filtered and evaporated. The residue was dissolved in toluene (100 ml), washed with water (3×25 ml), dried and evaporated. The residue (37 g, 172 mmol) was dissolved in dichloromethane (50 ml) and chlorosulfonic acid (93 g, 800 mmol) was added slowly at −10° C. The reaction mixture was stirred at room temperature for 1 h. Ice water (25 ml) was added carefully and the mixture was extracted with dichloromethane (3×100 ml). The combined organic phases were washed with water, dried and evaporated to give crude (4-chlorosulfonyl-2-chloro-phenoxy)-acetic acid ethyl ester as an oil in 47.5 g yield.
Workup
- filtrationThe reaction mixture was filtered
- customevaporated
- dissolutionThe residue was dissolved in toluene (100 ml)
- washwashed with water (3×25 ml)
- customdried
- customevaporated
- extractionthe mixture was extracted with dichloromethane (3×100 ml)
- washThe combined organic phases were washed with water
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-31654257421f49b68a9ba90653f0d685
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129268B2
Reaction notes
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