ETHYL(5-BROMOBENZOFURAN)-2-CARBOXYLATE Chemical Properties

Melting point:

60-62°

Boiling point:

328.3±22.0 °C(Predicted)

Density 

1.520±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

Appearance

White to off-white Solid

InChI

InChI=1S/C11H9BrO3/c1-2-14-11(13)10-6-7-5-8(12)3-4-9(7)15-10/h3-6H,2H2,1H3

InChIKey

XLJWAHXKBCDQNP-UHFFFAOYSA-N

SMILES

O1C2=CC=C(Br)C=C2C=C1C(OCC)=O

CAS DataBase Reference

84102-69-2

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2932990090

ETHYL(5-BROMOBENZOFURAN)-2-CARBOXYLATE Usage And Synthesis

Uses

Ethyl 5-bromobenzofuran-2-carboxylate

Synthesis

5-Bromosalicylaldehyde (5 g, 25 mmol, 1.0 eq.) and cesium carbonate (8.2 g, 25 mmol, 1.0 eq.) were dissolved in 80 ml of DMF and stirred well. Subsequently, ethyl bromoacetate (8.3 g, 50 mmol, 2.0 eq.) was slowly added to the reaction system. The reaction mixture was stirred at room temperature for 30 min. After that, the reaction temperature was increased to 120 °C for 2 hours. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and poured into ice water and stirred vigorously for 30 minutes. The precipitate was collected by filtration, the filter cake was washed with water and dried to give the yellow powdery solid product ethyl 5-bromobenzofuran-2-carboxylate (4 g, 59.7% yield).

References

[1] Patent: CN106478564, 2017, A. Location in patent: Paragraph 0216; 0217; 0218
[2] Patent: CN107383024, 2017, A. Location in patent: Paragraph 0473
[3] Patent: US2004/209865, 2004, A1
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5591 - 5593

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