Hydrogen Bromide → Methyl 3alpha-acetoxy-6-bromo-7-keto-5beta-cholanoate

Participants

Reaction Steps

A solution of methyl 3α-acetoxy-7-keto-5β-cholanoate (5.6 g, 12.54 mmoles) in acetic acid (100 ml) was added with a bromine solution (2.8 g) in acetic acid (10 ml) and immediately after with 48% hydrobromic acid (0.74 ml). The resulting reaction mixture was left to react overnight under strong magnetic stirring, then it was poured into water (300 ml) and filtered under vacuum to obtain a solid (8,03 g) which was subjected to flash chromatography on silica, eluting with methylene chloride/methanol 99.5:0.5, to yield 6.0 g of a pure product (91%).

Provenance & Evidence