Synthesis
General procedure for the synthesis of 2-iodo-1,3-dimethylbenzene using 2,6-dimethylphenylboronic acid as starting material: arylboronic acid (0.5 mmol) and K2CO3 (1 mmol, 138.0 mg) were added to a 20 mL Schlenk tube fitted with a non-magnetic stir bar. The reaction tube was evacuated and filled with nitrogen and this operation was repeated twice. Acetonitrile (2 mL) and iodine (0.75 mmol, 191 mg) were added to the reaction tube at room temperature. The reaction tube was sealed and placed in an oil bath preheated to 80 °C for 8-12 h under nitrogen protection. Upon completion of the reaction, the reaction solution was cooled to room temperature. Water (10 mL) was added for dilution. For the products 2s and 2t, the pH needed to be adjusted to 2 by adding 1 M HCl to the aqueous phase before extraction. the aqueous phase was extracted with ethyl acetate (3 x 5 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated by rotary evaporation. Finally, the residue was purified by silica gel column chromatography to give the target products 2a-v.
References
[1] Synlett, 2014, vol. 25, # 7, p. 995 - 1000
