General procedure for the synthesis of ethyl 3-phenoxybenzoate from ethyl 3-hydroxybenzoate and phenylboronic acid:
1. Intermediate 72- Preparation of ethyl 3-phenoxybenzoate. Ethyl 3-hydroxybenzoate (0.200 g, 1.20 mmol), phenylboronic acid (0.294 g, 2.41 mmol), copper acetate (0.437 g, 2.41 mmol) and pyridine (0.195 mL, 2.42 mmol) were dissolved in dichloromethane (8 mL) and the reaction was stirred at room temperature overnight.
2. After the reaction was completed, the reaction mixture was filtered and the filtrate was concentrated in vacuum to remove the solvent.
3. The crude product was purified by fast chromatography on silica gel with the eluent being a 5% to 35% heptane solution of ethyl acetate to give 0.222 g (76% yield) of the target compound, ethyl 3-phenoxybenzoate, as a colorless oil. 4. The structure of the product was determined by 1H NPLC.
4. The structure of the product was confirmed by 1H NMR (DMSO-d6): δ 7.73 (d, 1H), 7.52 (t, 1H), 7.44-7.41 (m, 3H), 7.31 (dd, 1H), 7.21 (t, 1H), 7.07 (d, 2H), 4.29 (q, 2H), 1.29 (t, 3H).
