Uses
4-(Bromomethyl)pyridine hydrobromide may be used in the preparation of:
- 3-(4-pyridylmethyl)-2′,3′-di-O-oleyl-5′-O-(4,4′-dimethoxytriphenylmethyl)uridine
- 3-(4-pyridylmethyl)-3′-O-oleyl-5′-O-(4,4-dimethoxytriphenylmethyl)-thymidine
- 1,4-bis(N-hexyl-4-pyridinium)butadiene diperchlorate
It may also be used in the preparation of the following benzoxazine derivatives:
- 2-morpholin-4-yl-7-(pyridin-4-ylmethoxy)-4H-1,3-benzoxazin-4-one
- 8-methyl-2-morpholin-4-yl-7-(pyridin-4-ylmethoxy)-4H-1,3-benzoxazin-4-one
- 2-morpholin-4-yl-8-(pyridin-4-ylmethoxy)-4H-1,3-benzoxazin-4-one
General Description
4-(Bromomethyl)pyridine hydrobromide is a substituted pyridine. It reacts with 1,2-ethanediamine and 1,3-propanediamine to form the corresponding diamines.
Synthesis
General procedure for the synthesis of 4-(bromomethyl)pyridine hydrochloride from 4-pyridinemethanol: To a 30 mL chloroform solution of 4-pyridinemethanol (3 g, 27.5 mmol) was added phosphorus pentabromide (5.93 g, 13.7 mmol). The reaction mixture was refluxed for 1 hour. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the resulting crude product was recrystallized in ethanol to afford 4-(bromomethyl)pyridine hydrochloride as a white solid (4.05 g, 58.1% yield). Electrospray mass spectrometry (positive ion mode) showed m/e = 173 ([M + H]+).
References
[1] Patent: US6403792, 2002, B1
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 38, p. 11640 - 11644
[3] Angew. Chem., 2017, vol. 129, # 38, p. 11799 - 11803,5
[4] Patent: US2010/152160, 2010, A1. Location in patent: Page/Page column 81
[5] Chemical Communications, 2011, vol. 47, # 5, p. 1482 - 1484
