3-Bromo-1-benzothiophene

Chemical Properties

Colorless to yellow to red liquid

Uses

3-Bromothianaphthene may be used in the synthesis of (benzo[b]thiophen-3-yl)trimethylstannane.

Uses

Antifungal activity of synthetic di (hetero) arylamines based on the benzo [b] thiophene moiety.

General Description

3-Bromothianaphthene is a heteroaryl halide. It undergoes Suzuki-Miyaura reaction with phenylboronic acid (PBA) or 3-thienylboronic acid in the presence of a novel heterogeneous Pd catalyst [Pd@PDEB, PDEB=poly(1,3-diethynylbenzene)]. The substitution reaction of 3-bromothianaphthene with piperidine to form 3-piperidinothianaphthene as the major product has been reported.

Synthesis

The general procedure for the synthesis of 3-bromobenzothiophene from 2,3-dibromothiophene was as follows: first, the halogenated heterocycle (0.66 mmol) was dissolved in anhydrous THF (13.2 mL) and degassed by drumming in argon for a few minutes. Subsequently, PdCl2 (dppf) (27.0 mg, 0.033 mmol, 5.0 mol%), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were added sequentially. The reaction mixture was stirred at room temperature for appropriate time under argon protection and finally post-treated according to standard methods.

References

[1] Journal of Organic Chemistry, 2012, vol. 77, # 21, p. 9921 - 9925,5
[2] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209
[3] Patent: WO2015/188790, 2015, A1. Location in patent: Page/Page column 22