Benzofuran

Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the structural nucleus (parent compound) of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.

There are benzofuran based herbicides: ethofumesate and benfuresate.[1] Several psychoactive drugs such as 5-MAPB and 6-APB are also derived from benzofuran.

## Contents

* 1 Production
* 1.1 Laboratory methods
* 2 Related compounds
* 3 References

## Production

Benzofuran is extracted from coal tar. It is also obtained by dehydrogenation of 2-ethylphenol.[2]

### Laboratory methods

Benzofurans can be prepared by various methods in the laboratory. Notable examples include:

* O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration (cyclication) of the resulting ether and decarboxylation.[3]

* Perkin rearrangement, where a coumarin is reacted with a hydroxide:[4][5][6]

* Diels–Alder reaction[clarification needed] of nitro vinyl furans with various dienophiles:[7]

* Cycloisomerization of alkyne ortho-substituted phenols:[8]

## Related compounds

* Substituted benzofurans
* Dibenzofuran, an analog with a second fused benzene ring.
* Furan, an analog without the fused benzene ring.
* Indole, an analog with a nitrogen instead of the oxygen atom.
* Benzothiophene, an analog with a sulfur instead of the oxygen atom.
* Isobenzofuran, the isomer with oxygen in the adjacent position.
* Aurone
* Thunberginol F

## References

1. ↑ "Classification of herbicides" (in en). https://bcpcpesticidecompendium.org/class_herbicides.html.
2. ↑ Collin, G.; Höke, H. (2007). Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.l03_l01. ISBN 978-3527306732.
3. ↑ Burgstahler, A. W.; Worden, L. R. (1966). "Coumarone". Organic Syntheses 46: 28. https://www.orgsyn.org/Content/pdfs/procedures/cv5p0251.pdf. ;  Collective Volume, 5, pp. 251
4. ↑ Perkin, W. H. (1870). "XXIX. On some New Bromine Derivatives of Coumarin". Journal of the Chemical Society 23: 368–371. doi:10.1039/JS8702300368. https://zenodo.org/record/2126035.
5. ↑ Perkin, W. H. (1871). "IV. On some New Derivatives of Coumarin". Journal of the Chemical Society 24: 37–55. doi:10.1039/JS8712400037. https://zenodo.org/record/1848365.
6. ↑ Bowden, K.; Battah, S. (1998). "Reactions of Carbonyl Compounds in Basic Solutions. Part 32. The Perkin Rearrangement". Journal of the Chemical Society, Perkin Transactions 2 1998 (7): 1603–1606. doi:10.1039/a801538d.
7. ↑ Kusurkar, R. S.; Bhosale, D. K. (1990). "Novel Synthesis of Benzosubstituted Benzofurans Via Diels-Alder Reaction". Synthetic Communications 20 (1): 101–109. doi:10.1080/00397919008054620.
8. ↑ Fürstner, Alois; Davies, Paul (2005). "Heterocycles by PtCl2-Catalyzed Intramolecular Carboalkoxylation or Carboamination of Alkynes". Journal of the American Chemical Society 127 (43): 15024–15025. doi:10.1021/ja055659p. PMID 16248631.

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