Potassium Carbonate → Methyl 2-(4-acetyl-2-(3-trifluoromethylphenyl)phenoxy)acetate

Participants

Reaction Steps

Methyl 2-(4-acetyl-2-bromophenoxy)acetate (16) (710 mg, 2.5 mmol, 1 eq), 3-(trifluoromethyl)phenylboronic acid (709 mg, 3.75 mmol, 1.5 eq, Aldrich, Milwaukee, Wis., USA) and tetrakis(triphenylphosphine) palladium (100 mg, 0.086 mmol, 0.03 eq) were dissolved in t-BuOH (1 mL) and K2CO3 (1 mL of a 4 M solution in H2O) and heated in a microwave at 120° C. for 20 min. The resultant reaction mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The obtained residue was purified via silica gel chromatography (20% EtOAc/hexane) to give 650 mg (74%) of methyl 2-(4-acetyl-2-(3-trifluoromethylphenyl)phenoxy)acetate (17) as white solid. 1HNMR (CDCl3, 400 MHz): δ 8.43 (s, 2H), 7.90 (m, 2H), 7.60 (m, 2H), 6.89 (d, 1H), 4.72 (s, 2H), 3.79 (s, 3H), 2.59 (s, 3H). MS (ES-API): M+1=353.1. HPLC (Method B) tR=3.28 min.

Provenance & Evidence