Ethyl 2-thenoate → Ethyl 4-nitrothiophene-2-carboxylate
Reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]>S(=O)(=O)(O)O>[N+:1]([C:13]1[CH:12]=[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:10][CH:14]=1)([O-:4])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of nitric acid/sulfuric acid (1:2.5) was added dropwise to a stirred solution (2.7 M) of ethyl 2-thiophene carboxylate in sulfuric acid at −10° C. After stirring for an additional half an hour, the reaction mixture was poured into ice-water. The resulting precipitate was filtered, washed with water and dried to give the title compound (96%) as a mixture 1:1 of 4-nitro and 5-nitro regioisomers.
Workup
- filtrationThe resulting precipitate was filtered
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-89cf60e7883645b18bcd89b4b2e377f0
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07781431B2
Reaction notes
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