Iodine → HCID 66639685, compound

Participants

Reaction Conditions

Reaction Steps

A dry and nitrogen-flushed 10-ml-Schlenk-flask, equipped with a magnetic stirring bar and a septum, was charged with a solution of the di-tert-butyl isophthalate (278 mg, 1 mmol) in dry THF (1 ml). After cooling to 0° C., a freshly prepared (TMP)2Mg.2LiCl solution (0.6 mol/l in THF, 1.83 ml, 1.1 mmol) was added dropwise and the reaction mixture was stirred at the same temperature. The completion of the metalation (2 h) was checked by GC-analysis of reaction aliquots quenched with a solution of I2 in dry ether. Iodine (508 mg, 2 mmol) dissolved in dry THF (2 ml) was then added at 0° C. and the resulting mixture warmed to room temperature. After stirring for 1 hour, the reaction mixture was quenched with sat. aq. Na2S2O3, extracted with ether (3×20 ml) and dried over Na2SO4. After filtration the solvent was removed in vacuo. Purification by flash-chromatography (n-pentane/diethyl ether, 10:1) furnished compound 51a (380 mg, 94%) as a yellow oil.

Provenance & Evidence