ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE Chemical Properties

Melting point:

245 °C(Solv: ethanol (64-17-5))

Boiling point:

476.7±45.0 °C(Predicted)

Density 

1.608±0.06 g/cm3(Predicted)

storage temp. 

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

pka

12.56±0.30(Predicted)

Appearance

Off-white to light yellow Solid

ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE Usage And Synthesis

Uses

Ethyl 5-Bromo-3-formyl-1h-indole-2-carboxylate is a versatile building block. It was used as a reactant in the synthetic preparation of hydroxyindolecarboxylates by Baeyer-Villiger oxidation.

Synthesis

Oxalyl chloride (3.43 mL, 39.9 mmol) was slowly added dropwise to a mixed solution containing DMF (30 mL) and dichloromethane (80 mL) at 0 °C while maintaining stirring. After the dropwise addition was completed, stirring was continued at 0 °C for 20 min. Subsequently, a solution of ethyl 5-bromoindole-2-carboxylate (10 g, 37.3 mmol) dissolved in DMF (80 mL) was added. The reaction mixture was transferred to room temperature and stirred continuously for 24 hours. Upon completion of the reaction, the mixture was poured into saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic phases were combined, washed sequentially with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Finally, the target product ethyl 5-bromo-3-formyl-1H-indole-2-carboxylate was obtained by ethanol recrystallization in a yield of 8.9 g and 81%.

References

[1] Patent: WO2006/77366, 2006, A1. Location in patent: Page/Page column 152
[2] Patent: WO2006/77367, 2006, A1. Location in patent: Page/Page column 89

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