Sulfuric Acid → 2-Iodo-4-(6-(trifluoromethyl)pyridin-3-yl)phenol

Participants

Reaction Steps

4-(6-(Trifluoromethyl)pyridin-3-yl)phenol (Preparation 61, 1.24 g, 5.18 mmol) was dissolved in a mixture of acetic acid (10 mL), dichloromethane (10 mL) and CH3CN (10 mL) at room temperature. Concentrated sulphuric acid (0.5 mL) was then added followed by N-iodosuccinimide (1.052 g, 4.67 mmol). The reaction was stirred at room temperature for 18 hours. A further aliquot of N-iodosuccinimide (116 mg, 0.518 mmol) was added and the reaction mixture was stirred for one hour and concentrated in vacuo. The crude oil was purified on silica gel by Biotage™ (5% to 60% of EtOAc in heptane over 20 CV) and fractions containing product were evaporated to give an inseparable mixture of product/starting material 7:3 (840 mg). This was used directly in the next stage without further purification.

Provenance & Evidence