Bromoacetic Acid → 1-(Methylsulfonyl)-2-nitrobenzene
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([OH:12])=[O:11])([O-:3])=[O:2].Br[CH2:14]C(O)=O.[OH-].[Na+]>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([CH3:14])(=[O:12])=[O:11])([O-:3])=[O:2]Participants
4
Procedure
This is contradicted by investigations by A. Courtin, H. -R. von Tobel and G. Auerbach, Helv. Chim. Acta 63, 1412 (1980), according to which, on heating of 1 mol of 2-nitrobenzenesulfinic acid, 2 mol of bromoacetic acid and 2 mol of sodium hydroxide solution under reflux conditions for 24 hours, only methyl 2-nitrophenyl sulfone is obtained in 91% yield. Evidently, the carboxymethyl aryl sulfone forming is immediately decarboxylated to the methyl aryl sulfone under the acidic reaction conditions.
Sources & evidence
- ORD record
- ord-af080897036847128303fed38b0c1847
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05101047
Reaction notes
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