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The synthesis of 14C-methylene diiodide and 14C-propane-1,3-dibromide

✍ Scribed by A. R. Jones

Publisher
John Wiley and Sons
Year
1975
Tongue
French
Weight
165 KB
Volume
11
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Existing methods have been adapted for the small scale synthesis of the title compounds in high yield. Modification of the iodoform reaction enables 1,3‐^14^C‐acetone (I) to be converted in over 95% yield to ^14^C‐iodoform (II) which is reduced by sodium aresenite to ^14^C‐methylene diiodide (III). Lithium aluminium hydride reduction of ^14^C‐diethyl malonate (IV) to ^14^C‐propane‐1, 3‐diol (V), followed by acetylation and displacement with hydrobromic acid, produces ^14^C‐propane‐1,3‐dibromide (VII) in 87% overall yield. The use of u‐. 2‐ or 1,3‐^14^C–diethyl malonate enables propane ‐1,3‐dibromide to be synthesised in any desired labelling pattern. Compounds III V and VII are useful difunctional 1‐ and 3‐carbon intermediates for further radioactive syntheses.

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