ethyl 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate Chemical Properties

Boiling point:

398.8±37.0 °C(Predicted)

Density 

1.692±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

13.72±0.30(Predicted)

Appearance

Light yellow to yellow Solid

Water Solubility 

Sparingly soluble in water.

InChI

InChI=1S/C9H8BrNO2S/c1-2-13-9(12)6-3-7-5(11-6)4-8(10)14-7/h3-4,11H,2H2,1H3

InChIKey

KXGSKTSSCQBDOA-UHFFFAOYSA-N

SMILES

N1C(C(OCC)=O)=CC2SC(Br)=CC1=2

ethyl 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate Usage And Synthesis

Uses

Ethyl 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate is used as an important raw material in organic synthesis.

Synthesis

Under argon protection, 5-bromo-2-thiophenecarboxaldehyde (19.1 g, 0.1 mol) and ethyl azidoacetate (51.6 g, 0.4 mol) were dissolved in anhydrous ethanol (800 mL) in a 2 L four-necked flask and the air in the reaction system was displaced by a stream of argon gas. An ethanolic solution of sodium mass ethanolate (136 g, 0.4 mol) was slowly added dropwise to the above mixed solution under the condition of cooling to 0 °C in an ice bath, followed by stirring the reaction for 2 hours at 0 °C. After completion of the reaction, saturated aqueous ammonium chloride solution was added to adjust the reaction solution to weak acidity (pH ≈ 6). Then, appropriate amount of water was added to dilute the reaction mixture, and the precipitate precipitated was collected by filtration and dried to obtain ethyl 2-azido-3-(5-bromo-2-thienyl)-acrylate as a yellow solid (yield: 18.4 g, yield: 61.3%). Next, ethyl 2-azido-3-(5-bromo-2-thienyl)-acrylate (18.1 g, 60 mmol) was transferred to a 500 mL aubergine flask, dissolved in o-xylene (200 mL), heated to reflux and stirred for 1.5 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure and the resulting crude product was purified by recrystallization (solvent: hexane/ethyl acetate mixture). The crystalline product was collected by filtration and dried to give ethyl 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate (d-1) (Yield: 12.1 g, Yield: 73.8%).

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

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