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The synthesis of 14 C‐methylene diiodide and 14 C‐propane‐1,3‐dibromide
Author(s) -
Jones A. R.
Publication year - 1975
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590110111
Subject(s) - chemistry , propane , yield (engineering) , malonate , medicinal chemistry , methylene , hydrobromic acid , ethylene dibromide , diol , acetone , lithium aluminium hydride , diethyl malonate , organic chemistry , catalysis , toxicology , materials science , metallurgy , biology
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.