3-Bromo-1-(triisopropylsilyl)pyrrole

Uses

3-Bromo-1-(triisopropylsilyl)pyrrole is a pyrrole analogue mainly used in the field of organic synthesis. It can be used to prepare other heterocyclic compounds such as 1-(triisopropylsilyl)pyrrole and 3-Butadienyl-1-tosylpyrroles.

Synthesis

General procedure for the synthesis of 3-bromo-1-(triisopropylmethylsilyl)pyrrole from 1-(triisopropylmethylsilyl)pyrrole: at -78 °C, N-bromosuccinimide (NBS, 3.25 g, 18.3 mmol) was slowly added to a 1-(triisopropylmethylsilyl)pyrrole (3.72 g, 16.6 mmol) solution of tetrahydrofuran (THF, 17 mL ) solution was maintained at temperature and stirred continuously for 5 hours. Upon completion of the reaction, hexane (15 mL) and pyridine (0.5 mL) were added to the mixture and stirring was continued for 5 minutes. Subsequently, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=30:1) to finally obtain 3-bromo-1-(triisopropylmethylsilyl)pyrrole (4.67 g, 93% yield) as a colorless oil.

References

[1] Chemische Berichte, 1989, vol. 122, p. 169 - 174
[2] Tetrahedron, 2011, vol. 67, # 35, p. 6673 - 6678
[3] Journal of Organic Chemistry, 1984, vol. 49, # 17, p. 3239 - 3240
[4] Tetrahedron, 2004, vol. 60, # 34, p. 7141 - 7146
[5] Organic Letters, 2014, vol. 16, # 24, p. 6334 - 6337