A stirred suspension of 4-tert-butyl-2-bromobenzoic acid (0.26 g, 1.0 mmol), 4-fluoro phenol (0.22 g, 2.0 mmol), cesium carbonate (0.65 g, 2.0 mmol), copper trifluoromethanesulfonate-benzene complex (13 mg, 25 μmol), 1-naphthoic acid (0.34 g, 2.0 mmol), and 4 Å molecular sieves (0.25 g) in toluene (10 mL) and EtOAc (5 μL) was heated at 110° C. for 16 h. The reaction was concentrated under reduced pressure and purified by silica gel chromatography (0%-5% MeOH—CH2Cl2) to afford 2-(4-fluorophenoxy)-4-tert-butylbenzoic acid (0.11 g, 39% yield) as a white solid. LC/MS: m/z 289.0 (M+H)+ at 3.58 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, CDCl3) δ 8.12 (d, J=8.3 Hz, 1H), 7.24 (d, J=1.7 Hz, 1H), 7.14-7.05 (m, 4H), 6.84 (d, J=1.6 Hz, 1H), 1.23 (s, 9H) ppm.
