3-(Trifluoromethyl)phenol → 2-(3-(Trifluoromethyl)phenoxy)-3-pyridinecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-nicotinic acid (1.0 g, 6.35 mmol, 1.0 equiv; [CAS RN 2942-59-8]) and 3-trifluoromethyl-phenol (1.03 g, 6.35 mmol, 1.0 equiv; [CAS RN 98-17-9]) in anhydrous DMF (5 mL) was added potassium carbonate (1.75 g, 12.69 mmol, 2.0 equiv; [CAS RN 584-08-7]), copper(I) iodide (0.12 g, 0.64 mmol, 0.1 equiv; [CAS RN 7681-65-4]) and copper(0) nanopowder with an averaged particle size of 100 nm (0.12 g, 1.90 mmol, 0.3 equiv; [CAS RN 7440-50-8]). The reaction mixture was heated by microwave irradiation to 140° C. for 30 min. The solvent was evaporated under reduced pressure and the crude reaction product taken up in water (25 mL) and filtered. The solution was adjusted to pH 4 by addition of acetic acid and the formed white precipitate filtered, washed with little cold water and dried under high vacuum providing 0.53 g (28%) of the title compound. 1H NMR (300 MHz, DMSO): δ7.26-7.30 (m, 1H), 7.43-7.50 (m, 2H), 7.57-7.66 (m, 2H), 8.26-8.29 (m, 2H). 19F NMR (282 MHz, DMSO): δ−61.0. MS (ISN): 282.1 [M−H]−.

Provenance & Evidence