N-bromobutanimide → Methyl 4-hydroxythiophene-3-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]([OH:10])[CH2:7][S:8][CH:9]=1)=[O:4].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:10])=[CH:7][S:8][CH:9]=1)=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1.6 parts of 3-hydroxy-dihydrothiophene-4-carboxylic acid methyl ester are introduced into 15 parts by volume of carbon tetrachloride and the mixture is cooled to 0° C. 1.78 parts of N-bromosuccinimide are added in portions over 30 minutes and the mixture is kept for one hour at 0° C. The end product is isolated from the reaction mixture analogously to Example 5c. 1.2 parts (76% of theory) of 3-hydroxythiophene-4-carboxylic acid methyl ester of melting point 40°-43° C. are obtained.
Workup
- customThe end product is isolated from the reaction mixture analogously to Example 5c
Sources & evidence
- ORD record
- ord-fc82306ef72044cfa99f0303cdcefc6e
- Source dataset
- uspto-grants-1980_12
- Patent number
- US04242518
Reaction notes
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