2-iodo-1,3-di(propan-2-yl)benzene

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5.09 g (17.7 mmol) of 2, 6-diisopropylphenyl iodide in 70 ml of dry ethyl ether was dropwise added 1.6M solution of n-butyllithium in hexane (11.1 ml, 17.8 mmol) at -20° C. The reaction mixture was allowed to warm at 0° C., stirred for 1 hour and poured onto about 100 g of pulverized dry ice. The mixture was allowed to warm gradually to room temperature, mixed with 50 ml of water and the aqueous layer was made alkaline with aqueous sodium hydroxide. The organic layer was separated, and the aqueous layer was washed with ethyl ether, acidified With conc. hydrochloric acid and extracted with ethyl ether. The extract was washed with saturated saline, dried over anhydrous magnesium sulfate, and the solvent evaporated to give 2.53 g of 2, 6-diisopropylbenzoic acid as white solid. at -20° C to warm gradually to room temperature The organic layer was separated the aqueous layer was washed with ethyl ether extracted with ethyl ether The extract was washed with saturated saline dried over anhydrous magnesium sulfate the solvent evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 7.09 g (40 mmol) of 2, 6-diisopropylaniline in 54 ml of water and 18 ml of conc. hydrochloric acid was dropwise added a solution of 2.76 g (40 mmol) of sodium nitrite in 16 ml of water with sufficient stirring and ice cooling, and the resultant mixture was stirred for further 10 minutes. A solution of 6.64 g (40 mmol) of potassium iodide in 6 ml of water was added to the mixture, and the mixture was stirred for 4 hours at room temperature and refluxed with heating for 1 hour. After cooling, the reaction mixture was extracted with hexane, and the extract was washed with aqueous sodium nitrite and saturated saline in this order, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was chromatographed on a silica gel column, eluting with hexane to give 5.09 g of 2, 6-diisopropylphenyl iodide as an oil. the mixture was stirred for 4 hours at room temperature refluxed with heating for 1 hour After cooling the reaction mixture was extracted with hexane the extract was washed with aqueous sodium nitrite and saturated saline in this order dried over anhydrous magnesium sulfate the solvent evaporated The residue was chromatographed on a silica gel column eluting with hexane