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Bromination of 2,1,3‐benzothiadiazoles
Abstract
The bromination of 2,1,3‐benzothiadiazoles in 47% hydrobromic acid at elevated temperature has led to a general preparative method for the synthesis in high yield of otherwise difficulty accessible brominated 2,1,3‐benzothiadiazoles. The typical addition reaction is apparently eliminated under these reaction conditions and substitution takes place exclusively. Bromination of 2,1,3‐benzothiadiazole occurs successively at positions 4 and 7. 4‐Substituted 2,1,3‐benzothia‐diazoles are selectively brominated at position 7. 5‐Bromo‐ and 5‐methyl‐2,1,3‐benzothiadiazole are brominated consecutively at positions 4 and 7.
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Citations
Cited by
Coffin, R. C., Peet, J., Rogers, J., & Bazan, G. C. (2009) · Nature Chemistry · doi:10.1038/nchem.403 · Cited by 597
Albrecht, S., Janietz, S., Schindler, W., Frisch, J., Kurpiers, J., Kniepert, J., Inal, S., Pingel, P., Fostiropoulos, K., Koch, N., et al. (2012) · Journal of the American Chemical Society · doi:10.1021/ja305039j · Cited by 374
Neto, B. A. D., Lapis, A. A. M., da Silva Júnior, E. N., & Dupont, J. (2013) · European Journal of Organic Chemistry · doi:10.1002/ejoc.201201161 · Cited by 328
Metadata
- Authors
- Pilgram, K., Zupan, M., & Skiles, R.
- Venue
- Journal of Heterocyclic Chemistry
- Publisher
- Wiley
- Published
- 1970-06
- Volume
- 7
- Issue
- 3
- Pages
- 629-633
- ISSN
- 0022-152X (ISSN-L)
- 1943-5193
- OpenAlex
- W2036242529
- Cited by
- 215
- References
- 0
- FWCI
- 2.18
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Bromination of 2,1,3‐benzothiadiazoles. https://app.cochat.ai/papers/10.1002/jhet.5570070324
- The paper
- Pilgram, K., Zupan, M., & Skiles, R. (1970). Bromination of 2,1,3‐benzothiadiazoles. Journal of Heterocyclic Chemistry. https://doi.org/10.1002/jhet.5570070324
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
