Hydrochloric Acid → 3-Iodobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 mol %), 3-bromobenzoic acid (210 mg, 1.00 mmol), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. trans-N,N′-Dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol %), 1,1,1,3,3,3-hexamethyldisilazane (211 μL, 1.00 mmol), and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 23 h. The resulting suspension was allowed to reach room temperature, poured into 10% aq HCl (20 mL), and extracted with dichloromethane (3×15 mL). The combined organic phases were dried (Na2SO4) and concentrated. The residue was dissolved in dichloromethane (50 mL) and washed with an aqueous solution of 1% HCl and 1% Na2SO3. The aqueous phase was extracted with with dichloromethane (2×20 mL). The organic phases were combined, dried (Na2SO4) and concentrated. The solid residue was washed with hexane (3×15 mL) and dried to provide 3-iodobenzoic acid (222 mg, 90% yield) as white, fine needles.

Provenance & Evidence