Djerassi, Carl; Scholz, Caesar R. published the artcile< Brominations with pyridine hydrobromide perbromide, C5H5N.HBr.Br2>, Name: (9Z,12Z)-Methyl octadeca-9,12-dienoate, the main research area is PYRIDINE AND PYRIDINE COMPOUNDS.
Cholestanone (38 mg.) and 31 mg. C5H5N.HBr.Br2 (I) in 1 cc. AcOH at 40-60° give 81% of the 2-Br derivative; Me 3-ketoallo-etiocholanate and I give 75% of the 2-Br derivative; EtOH or a mixture of EtOH and CHCl3 could be used as the solvent. Me 3-keto-12-acetoxycholanate (110 mg.) and 75 mg. I in 5 cc. AcOH, warmed 1 min. to about 40°, give 61% of the 4-Br derivative; coprostanone gives the 4-Br derivative Me 3(α)-acetoxy-12-ketoetiocholanate (195 mg.) and 155 mg. I in 1.2 cc. AcOH, warmed until solution resulted and kept 2.5 hrs. at room temperature, give on saponification and rearrangement 74% 3(α),12-dihydroxy-11-ketoetiocholanic acid. Cholestanone (380 g.) and 640 mg. I give after 10 min. 73% of the 2,4-di-Br derivative 4-(1-Piperidyl)-2-butanone (65 mg.) in 1 cc. AcOH containing 41% HBr and 135 mg. I, warmed about 30 sec., give 55% 1-bromo-4-(1-piperidyl)-2-butanone-HBr, m. 157-8° (decomposition). C5H5N.Br2 proved disappointing as a brominating agent.
Journal of the American Chemical Society published new progress about Bromination. 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Name: (9Z,12Z)-Methyl octadeca-9,12-dienoate.
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