Methyl 4-broMo-5-chlorothiophene-2-carboxylate

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Methyl 4-broMo-5-chlorothiophene-2-carboxylate Basic information
Product Name:Methyl 4-broMo-5-chlorothiophene-2-carboxylate
Synonyms:Methyl 4-broMo-5-chlorothiophene-2-carboxylate;4-Bromo-5-chloro-2-thiophenecarboxylic acid methyl ester;2-Thiophenecarboxylic acid, 4-bromo-5-chloro-, methyl ester;4-broMo-5-chlorothiophene-2-carboxylate;methyl 4-bromo-5-chloro-2-thiophenecarboxyl;methyl 4-bromo-5-chloro-2-thiophenecarboxylate
CAS:1047630-72-7
MF:C6H4BrClO2S
MW:255.52
EINECS:
Product Categories:
Mol File:1047630-72-7.mol
Methyl 4-broMo-5-chlorothiophene-2-carboxylate Structure
Methyl 4-broMo-5-chlorothiophene-2-carboxylate Chemical Properties
Boiling point 293.9±35.0 °C(Predicted)
density 1.762±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
Methyl 4-broMo-5-chlorothiophene-2-carboxylate Usage And Synthesis
Synthesis
Methyl-5-chlorothiophene-2-carboxylate

35475-03-7

Methyl 4-broMo-5-chlorothiophene-2-carboxylate

1047630-72-7

General procedure for the synthesis of methyl 5-chloro-4-bromothiophene-2-carboxylate from methyl 5-chlorothiophene-2-carboxylate: To a 1 L round bottom flask was added aluminum chloride (11.32 g, 85 mmol) and methyl 5-chlorothiophene-2-carboxylate (10 g, 56.6 mmol) dissolved in chloroform (250 mL). Bromine (4.08 mL, 79 mmol) was added slowly and dropwise over 10 min. The reaction mixture was stirred at 25 °C for 6 h. The light orange reaction solution was washed with saturated sodium bicarbonate solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography [n-hexane/ethyl acetate, 9:1] to give the target product (12 g, 80% yield) as a white solid.LC-MS (ESI) m/z 256 ([M+H]+).

References[1] Patent: WO2008/98104, 2008, A1. Location in patent: Page/Page column 188
[2] Drugs of the Future, 2014, vol. 39, # 8, p. 541 - 546
Methyl 4-broMo-5-chlorothiophene-2-carboxylate Preparation Products And Raw materials
Raw materialsMethyl-5-chlorothiophene-2-carboxylate-->Chloroform-->Aluminum chloride
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