methyl 5-bromo-1H-pyrrole-2-carboxylate Chemical Properties

Melting point:

101-103 °C

Boiling point:

290.5±20.0 °C(Predicted)

Density 

1.674±0.06 g/cm3(Predicted)

storage temp. 

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

form 

Solid

pka

14.18±0.50(Predicted)

color 

White to off-white

InChI

InChI=1S/C6H6BrNO2/c1-10-6(9)4-2-3-5(7)8-4/h2-3,8H,1H3

InChIKey

ZYBOXSDTMZRWBC-UHFFFAOYSA-N

SMILES

N1C(Br)=CC=C1C(OC)=O

Safety Information

HS Code 

2933998090

methyl 5-bromo-1H-pyrrole-2-carboxylate Usage And Synthesis

Uses

Methyl 5-Bromo-1H-pyrrole-2-carboxylate is a chemical reagent used in pharmaceutical synthesis.

Synthesis

Synthesis of 5-bromo-1H-pyrrole-2-carboxylic acid methyl ester (53): 1H-pyrrole-2-carboxylic acid methyl ester (52; 10 g, 80 mmol) was dissolved in a solvent mixture of 800 mL tetrahydrofuran (THF) and 400 mL methanol (MeOH). The reaction mixture was cooled to 0 °C. N-bromosuccinimide (NBS; 15 g, 8.4 mmol) was added in 5 additions in batches over 1.5 hours. After addition, the reaction mixture was continued to be stirred at 0 °C for 2 hours. Upon completion of the reaction, the reaction mixture was concentrated and purified by silica gel column chromatography (eluent: 2% ethyl acetate/petroleum ether) to afford 4.3 g of 5-bromo-1H-pyrrole-2-carboxylic acid methyl ester 53 as a white solid in 26% yield.The LCMS analysis resulted in: m/z 206.0 [M + H] and a retention time t R = 1.50 min.

References

[1] Journal of the American Chemical Society, 2006, vol. 128, # 18, p. 6054 - 6055
[2] Chemistry - A European Journal, 2009, vol. 15, # 28, p. 6910 - 6919
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 16, p. 2574 - 2577
[4] Patent: WO2017/31213, 2017, A1. Location in patent: Paragraph 00361
[5] Patent: US2002/6943, 2002, A1

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