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by | Mar 16, 2018 | Hosta

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4-Bromoaniline is a compound where an aniline molecule is substituted with a bromine atom on the para position. Commercially available, this compound may be used as a building block, e.g. in the preparation of monobrominated biphenyl via the Gomberg-Bachmann reaction.[2]

Preparation

4-Bromoaniline can be made by reacting acetyl chloride-protected aniline with bromine.

Synthesized and purified p-bromoaniline

Reactions

One laboratory route to 1-bromo-4-iodobenzene involves the Sandmeyer reaction. 4-Bromoaniline is treated with concentrated sulfuric acid and sodium nitrite, then potassium iodide.[3]

References

  1. ^ 4-Bromoaniline, Chemblink.com
  2. ^ M. Gomberg and W. E. Bachmann (1941). "p-Bromobiphenyl". Organic Syntheses; Collected Volumes, vol. 1, p. 113.
  3. ^ Banerjee, M.; Shukla, R.; Rathore, R. (15 January 2009). "Synthesis, Optical, and Electronic Properties of Soluble Poly-p-phenylene Oligomers as Models for Molecular Wires". Journal of the American Chemical Society. 131 (5): 1780–1786. doi:10.1021/ja805102d. PMID 19146375.
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