Bromine → HCID 86734034, compound

Participants

Reaction Steps

4β-Bromo-3α-hydroxy-5α-pregnane-11,20-dione (945 mg) in dry methanol (70 ml.) at 10° was treated with a solution of bromine (0.125 ml.) in methanol (5 ml.) dropwise over 7 hours, at such a rate that the bromine colour was taken up during the addition. The reaction solution was then stirred at room temperature for 30 minutes until it became colourless, and it was then diluted with water (300 ml.) and the white precipitate was extracted into methylene chloride. The organic solution was washed with water, dried over sodium sulphate and evaporated to a white foam (1.2 g.) which was purified by preparative T.L.C. in ethyl acetate/benzene 1/3 the upper (major) band giving 660 mg. of a white solid which was triturated with ether to give title compound (580 mg.) as white crystals, m.p. 164°-166°, [α]D + 76° (c 1.35).

Provenance & Evidence