3-Thiophenecarboxylic acid, 5-bromo-, ethyl ester
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3-Thiophenecarboxylic acid, 5-bromo-, ethyl ester
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CAS No:
170355-38-1
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Formula:
C7H7BrO2S
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Chemical Name:
3-Thiophenecarboxylic acid, 5-bromo-, ethyl ester
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Synonyms:
3-Thiophenecarboxylic acid,5-bromo-,ethyl ester;Ethyl 2-bromo-4-thiophenecarboxylate;Ethyl 5-bromothiophene-3-carboxylate;5-Bromothiophene-3-carboxylic acid ethyl ester
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CAS No:
3-Thiophenecarboxylic acid, 5-bromo-, ethyl ester Basic Attributes
235.09828
235.10
DTXSID50571073
2934999090
3-Thiophenecarboxylic acid, 5-bromo-, ethyl ester Use and Manufacturing
20 g (147 mmol) of aluminium chloride are added portionwise to a solution of 10 g (67 mmol) of ethyl thiophene-3-carboxylate in 160 ml of dichloro- methane, cooled beforehand to 0oC. The reaction medium is warmed to room temperature and a solution of 4 ml (73 mmol) of bromine in 10 ml of dichloromethane is then added. After reaction for 50 minutes at room temperature, the reaction medium is poured into a water + ice mixture and extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and evaporated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with a 9/1 HEPTANE/ETHYL acetate mixture. 9 g (57percent) of ethyl 5-bromothiophene-3-carboxylate are obtained.In a round bottom flask, 10.0 g of the compound of the formula (IX) was dissolved in 100 mL of ethanol, and then 1.5 mL of concentrated sulfuric acid was added dropwise and the reaction was refluxed overnight.After the reaction is completed, the reaction system is cooled to room temperature, 30 mL of water is added, the mixture is extracted with chloroform three times, the organic phases are combined, the organic phase is dried over anhydrous sodium sulfate, the desiccant is removed by filtration, and the filtrate is concentrated.Column chromatography using ethyl acetate/petroleum ether (boiling range 60-90° C.) (volume ratio 1/20) as a developer column afforded 11.36 g of the compound of Formula (III) in 98percent yield.
Computed Properties
Molecular Weight:235.10
XLogP3:2.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:233.93501
Monoisotopic Mass:233.93501
Topological Polar Surface Area:54.5
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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3-Thiophenecarboxylic acid, 5-bromo-, ethyl ester
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