反应详情

温度

120 °C

p-Fluorotoluene (1.65 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol %) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120° C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 76 mg ethyl p-fluorophenylacetate was obtained by column chromatography, in a yield of 84%. 1HNMR (400 MHz, CDCl3) δ 1.23 (t, J=7.2 Hz, 3H), 3.58 (s, 2H), 4.12 (q, J=7.2 Hz, 2H), 6.98-7.03 (m, 2H), 7.23-7.26 (m, 2H); 13CNMR (100 MHz, CDCl3) δ 14.2, 40.5, 60.9, 115.3, 115.5, 129.8, 129.9, 130.8, 130.9, 160.8, 163.2, 171.5; HRMS (ESI) calcd. for C10H11FNaO2 [M+Na]: 205.0635. found: 205.0634. The ethyl p-fluorophenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60° C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 59 mg product p-fluorophenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 91%.

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