Iodine → HCID 21449903, compound

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Reaction Steps

To form a Grignard reagent, to 3.6 g. of magnesium metal and a crystal of iodine are added, all at once, 25 ml. of a solution of 9.0 g. dibromoethane and 25.0 g. of p-(4-neopentylphenoxy)-bromobenzene in 150 ml. of absolute tetrahydrofuran (THF). After initiating the Grignard reaction, the rest of the above THF solution is added dropwise to maintain gentle reflux. The (Grignard reagent) reaction mixture is thereafter refluxed for half an hour; cooled and to it is added, dropwise, a solution of 8.3 g. of 4-pyridine-carboxaldehyde in 20 ml. of absolute THF. The reaction mixture is then stirred overnight, decomposed with saturated ammonium chloride aqueous solution and 100 ml. ether added. The organic phase is separated, dried over anhydrous sodium sulfate, filtered, and evaporated under vacuum to dryness to yield a residue. The residue is chromatographed on silica gel, first with toluene as the eluent and subsequently with toluene containing increasing concentrations of chloroform. The desired fractions are collected and evaporated under vacuum to dryness to yield a residue. From the residue is crystallized (from ether) the title product, m.p. 120°-122° C.

Provenance & Evidence