Iodine → 16-Heptadecenyl chloride

Participants

Reaction Steps

This example illustrates a synthetic protocol for inventive compound no. 3522 (see above for chemical name and formula). To a suspension of magnesium (3.10 g, 129 mmol) and a crystal of iodine in THF (10 ml) was added 10-undecenyl bromide (see: Syn. Comm. 1984, 14, 591-597) (6.00 g, 25.8 mmol) in THF (20 ml) over 40 minutes. The resuling reaction mixture was stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 50 minutes to a suspension of copper iodide (0.50 g, 2.58 mmol) and 1-bromo-6-chloro hexane (6.00 ml, 40.0 mmol) in THF (20 ml) and stirred at 25° C. for 16 hours. Sulfuric acid (1.0M, 50 ml) was added, extracted with diethyl ether (2×60 ml) and the organic solvent was dried over magnesium sulfate and evaporated. The residue was distilled at 0.75 mmHg, resulting in 1.78 g of 16-heptadecenyl chloride as a colourless liquid (25% yield, b.p. 130°-135° C.).

Provenance & Evidence