5-Bromo-4-chlorothiophene-2-sulfonamide → 4-Chlorothiophene-2-sulfonamide
Reaction equation
Br[C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][C:3]=1[Cl:11]>CC(O)=O.[Zn]>[Cl:11][C:3]1[CH:4]=[C:5]([S:7]([NH2:10])(=[O:9])=[O:8])[S:6][CH:2]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
To a stirred solution of 5-bromo-4-chlorothiophene-2-sulfonamide (2.4 g, 8.7 mmol) in AcOH (20 mL) is added zinc dust (1.7 g, 26.0 mmol). The reaction mixture is heated to 120° C. for 6 hr. After 6 hr, the mixture is filtered and neutralized with 1 M NaOH. The aqueous layer is extracted with EtOAc (2×100 mL). The combined organic extracts are dried (Na2SO4), filtered and concentrated in vacuo. The crude product is chromatographed on silica gel, eluting with CH2Cl2 to afford the title compound (0.88 g, 52%).
Workup
- filtrationthe mixture is filtered
- extractionThe aqueous layer is extracted with EtOAc (2×100 mL)
- dry with materialThe combined organic extracts are dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product is chromatographed on silica gel
- washeluting with CH2Cl2
Sources & evidence
- ORD record
- ord-ee96dca7353343b0ab451e1a1c0600f7
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07084170B2
Reaction notes
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