Methyl-4,5-dibromo-2-furoate Chemical Properties

Melting point:

56.0 to 60.0 °C

Boiling point:

110°C/0.8mmHg(lit.)

Density 

1.992±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform, Dichloromethane, Ethyl Acetate, Methanol

form 

Solid

color 

Off White

Safety Information

HS Code 

2932190090

Methyl-4,5-dibromo-2-furoate Usage And Synthesis

Uses

Methyl 4,5-dibromo-2-furoate is an intermediate in the synthesis of 4-Amino-2-furancarboxylic Acid (A609680), which is the characteristic structural element of the Proximicins. Proximicin A, B and C, are novel aminofuran antibiotic and anticancer compounds isolated from marine strains of the actinomycete Verrucosispora.

Synthesis

Preparative Example 2-1 Synthesis of methyl 4,5-dibromofuran-2-carboxylate Procedure: a catalytic amount of oxalyl chloride (210 μL, 2.4 mmol) was added slowly and dropwise to a mixed solution of dichloromethane (5.0 mL) and N,N-dimethylformamide containing 4,5-dibromofuran-2-carboxylic acid (500 mg, 1.9 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour. Subsequently, the solvent was removed by distillation under reduced pressure, triethylamine (340 μL, 2.4 mmol) and methanol (4.0 mL) were added, and stirring was continued for 1 h at room temperature. Upon completion of the reaction, the solvent was again removed by distillation under reduced pressure, saturated aqueous sodium bicarbonate was added, and extraction was carried out with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried with anhydrous sodium sulfate. Finally, the solvent was removed by reduced pressure distillation to afford the target product methyl 4,5-dibromofuran-2-carboxylate (460 mg, 88% yield). The product was characterized by 1H-NMR (400 MHz, CDCl3) with chemical shifts δ (ppm) of 3.90 (s, 3H), 7.18 (s, 1H).

References

[1] Patent: US2006/160874, 2006, A1. Location in patent: Page/Page column 21
[2] Patent: WO2004/7504, 2004, A1. Location in patent: Page 54-55
[3] Patent: WO2008/98104, 2008, A1. Location in patent: Page/Page column 216-217
[4] Patent: US2016/168176, 2016, A1. Location in patent: Paragraph 0241; 0242

Methyl-4,5-dibromo-2-furoate(54113-41-6)Related Product Information

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