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Chemical Structure| 4701-17-1 Chemical Structure| 4701-17-1
Chemical Structure| 4701-17-1

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CAS No.: 4701-17-1

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Product Details of 5-Bromothiophene-2-carbaldehyde

CAS No. :4701-17-1
Formula : C5H3BrOS
M.W : 191.05
SMILES Code : C1=C(SC(=C1)Br)C=O
MDL No. :MFCD00005432
InChI Key :GFBVUFQNHLUCPX-UHFFFAOYSA-N
Pubchem ID :78428

Safety of 5-Bromothiophene-2-carbaldehyde

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 5-Bromothiophene-2-carbaldehyde

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 4701-17-1 ]
  • Downstream synthetic route of [ 4701-17-1 ]

[ 4701-17-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 4701-17-1 ]
  • [ 637-81-0 ]
  • [ 238749-50-3 ]
YieldReaction ConditionsOperation in experiment
12.1 g With sodium ethanolate In ethanol; o-xylene at 0℃; for 3.5 h; Inert atmosphere; Reflux Under an argon stream, 5-bromo-2-thiophenecarboxaldehyde (19.1 g, 0.1 mol) and ethyl azidoacetate (51.6 g, 0.4 mol) were dissolved in ethanol (800 mL) in a 2 L four-neck flask, and a 20percent by mass sodium ethoxide ethanol solution (136 g, 0.4 mol) was slowly added dropwise to the obtained solution at 0° C. in an ice bath, followed by stirring for 2 hours.
After the reaction ended, a saturated ammonium chloride aqueous solution was added thereto to adjust the pH to be weakly acidic.
Furthermore, water was added thereto, and the precipitate was collected by filtration, and dried, whereby ethyl 2-azido-3-(5-bromo-thiophen-2-yl)-acrylate was obtained as a yellow solid (obtained amount: 18.4 g, yield: 61.3percent).
Next, ethyl 2-azido-3-(5-bromo-thiophen-2-yl)-acrylate (18.1 g, 60 mmol) was put into a 500 mL egg-plant shaped flask, and dissolved in o-xylene (200 mL), followed by refluxing and stirring for 1.5 hours. After the solution after refluxing and stirring was concentration under reduced pressure, the obtained crude product was recrystallized (solution: hexane and ethyl acetate), then, the resultant product was subjected to suction filtration, and the obtained filtered material was dried, whereby ethyl 2-bromo-4H-thieno [3.2-b]pyrrole-5-carboxylate (d-1) was obtained (obtained amount: 12.1 g, yield: 73.8percent).
References: [1] Patent: US2015/158888, 2015, A1, . Location in patent: Paragraph 0075-0080.
[2] Chemistry - An Asian Journal, 2015, vol. 10, # 6, p. 1335 - 1343.
[3] Patent: US2016/271273, 2016, A1, . Location in patent: Paragraph 0289.
  • 2
  • [ 4701-17-1 ]
  • [ 238749-50-3 ]
References: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 215 - 217.
[2] Chemistry - An Asian Journal, 2013, vol. 8, # 12, p. 3123 - 3132.
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 5, p. 1673 - 1692.
  • 3
  • [ 5382-16-1 ]
  • [ 4701-17-1 ]
  • [ 207290-72-0 ]
YieldReaction ConditionsOperation in experiment
71% Reflux 5-Bromothiophene-2-carboxaldehyde was placed in a reactor, and water was added thereto. 4-Hydroxypiperidine (3 eq) was added to the reactor, and the mixture was stirred for tens of minutes or overnight under reflux. Immediately after completion of reaction, the reaction mixture was filtered through filter paper, and the filtrate was cooled for tens of minutes with a flow of water and then for several hours with ice. The precipitated crystals were recovered through filtration under suction and washed with cold water. The crystals were dried and dissolved in chloroform. The chloroform solution was dried over sodium sulfate anhydrate, and the dried solution was filtered through a silica gel pad. The filtrate was washed with chloroform until the color thereof became faint. The filtrate was concentrated under reduced pressure until the start of crystallization. n-Hexane was added to the mixture, and stirring was performed overnight at room temperature. The formed crystals were recovered through filtration, washed with n-hexane, and dried under reduced pressure, to thereby yield 5-(4-hydroxypiperidin-1-yl)-thiophene-2-carboxaldehyde. By use of 5-bromothiophene-2-carboxaldehyde (42.30 g) and 4-hydroxypiperidine (67.30 g), amine incorporation was performed according to Production Step 1, to thereby yield 5-(4-hydroxy-piperidin-1-yl)-thiophene-2-carboxaldehyde (yield: 33.00 g, 71percent). The thus-produced 5-(4-hydroxy-piperidin-1-yl)-thiophene-2-carboxaldehyde (10.56 g) and 3,4-dimethoxybenzyl cyanide (8.86 g) were subjected to condensation according to Production Step 2, to thereby yield (Z)-2-(3,4-dimethoxy-phenyl)-3-[5-(4-hydroxy-piperidin-1-yl)-thiophen-2-yl]-acrylonitrile (yield: 13.50 g, 73percent). The thus-produced (Z)-2-(3,4-dimethoxy-phenyl)-3-[5-(4-hydroxy-piperidin-1-yl)-thiophen-2-yl]-acrylonitrile (20.00 g) was dissolved in chloroform (650 mL), and the solution was reacted with pyridine (6.41 g) and bromoacetyl bromide (14.13 g) according to Production Step 3 (Method A), to thereby yield bromo-acetic acid 1-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl ester (yield: 23.00 g, 87percent). The thus-produced bromo-acetic acid 1-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl ester (2.30 g) was dissolved in chloroform (100 mL), and the solution was reacted with piperidine (533 mg) and triethylamine (658 mg) according to Production Step 4, to thereby yield the title compound (yield: 1.40 g, 60percent).
References: [1] Synlett, 1998, # 4, p. 383 - 384.
[2] Synthetic Communications, 2000, vol. 30, # 8, p. 1359 - 1364.
[3] Patent: EP2218719, 2010, A1, . Location in patent: Page/Page column 7-8.
 

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