5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER Chemical Properties

Melting point:

212-214 °C

Boiling point:

386.2±22.0 °C(Predicted)

Density 

1.629±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.46±0.30(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

773873-77-1

Safety Information

HS Code 

2933998090

5-BROMO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER Usage And Synthesis

Application

Methyl 5-bromoindole-3-carboxylic acid can be used as an organic synthesis intermediate. It can be prepared in two steps from 5-bromo-1H-indole as a reactant, or it can be obtained by one-step esterification of 5-bromo-1H-indole-3-carboxylic acid.

Synthesis

GENERAL METHOD: 4.0 g of 5-bromo-1H-indole-3-carboxylic acid was dissolved in 40 times the volume (400 mL) of methanol and a catalytic amount of concentrated sulfuric acid was slowly added. The reaction mixture was heated to reflux for 5 hours, followed by slow cooling to room temperature. Ice-cold water was added to the cooled mixture and the yellow solid was collected by filtration. The solid was recrystallized from ethanol to give methyl 5-bromo-indole-3-carboxylate (12b) as a yellow solid in 62% yield. The product characterization data were as follows: melting point: 210-212 °C; IR (KBr, cm-1): 3213, 3114, 2929, 1745; 1H NMR (400 MHz, CDCl3): δ 3.93 (3H, s, -OCH3), 7.28 (1H, d, J = 8.8 Hz, Ar-H), 7.35 (1H, m, Ar-H ), 7.91 (1H, d, J = 2.8 Hz, Ar-H), 8.32 (1H, s, Ar-H), 8.67 (1H, s, -NH); 13C NMR (400 MHz, CDCl3 + DMSO-d6): δ 49.93, 105.91, 112.88, 113.75, 122.40, 124.26, 126.65, 131.89, 134.33, 164.13; HRMS (m/z): calculated value C10H9NO2Br [M]+: 253.98112, measured value: 253.98102.

References

[1] Chemical Papers, 2018, vol. 72, # 6, p. 1369 - 1378

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