2-Bromopyridine Explained

2-Bromopyridine is an aryl bromide and isomer of bromopyridine with the formula BrC5H4N. It is a colorless liquid that is used as an intermediate in organic synthesis. It can be prepared from 2-aminopyridine via diazotization followed by bromination.[1]

Reactions

2-Bromopyridine reacts with butyllithium to give 2-lithiopyridine,[2] which is a versatile reagent.[3] Pyrithione can be prepared in a two-step synthesis from 2-bromopyridine by oxidation to the N-oxide with a suitable peracid followed by substitution using either sodium dithionite or sodium sulfide with sodium hydroxide to introduce the thiol functional group.[4]

Applications

Organometallic addition to benzophenone followed by catalytic hydrogenation is the synthesis of pipradrol.

References

  1. Allen, C. F. H.; Thirtle, John R. "2-Bromopyridine" Organic Syntheses 1946, volume 26, pp. 16-18.
  2. 10.15227/orgsyn.088.0079. Synthesis of Lithium 2-Pyridyltriolborate and ITS Cross-Coupling Reaction with Aryl Halides. Organic Syntheses. 2011. 88. 79. Yasunori . Yamamoto. Juugaku. Sugai. Miho. Takizawa. Norio Miyaura. Norio. Miyaura. free.
  3. Satinder V. Kessar, Paramjit Singh, Dmitry Zuev, Zhenlei Song, Ya Wu "2-Lithiopyridine" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2015.
  4. Encyclopedia: 1-Hydroxypyridine-2(1H)-thione. David W.. Knight. Jens. Hartung. 1-Hydroxypyridine-2(1H)-thione. 15 September 2006. 10.1002/047084289X.rh067.pub2. John Wiley & Sons. Encyclopedia of Reagents for Organic Synthesis. 0471936235.

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