A kind of preparation method of deuterated aromatic compound

[0037] Embodiment 1: the preparation method of 2-deuterated-4-hexyltoluene

[0038]Palladium acetate (44.9 mg, 0.2 mmol), triphenylphosphine (52.4 mg, 0.2 mmol), sodium deuteroformate (276 mg, 4 mmol), norbornene (188 mg, 2 mmol), phosphoric acid were successively added to the 25 mL eggplant flask. Potassium (2.544 g, 12 mmol), potassium acetate (392 mg, 4 mmol), 2-iodotoluene (436 mg, 2 mmol), bromohexane (1.32 g, 8 mmol) and dimethylformamide (10 ml). High-purity nitrogen was replaced three times, and after 16 hours of reaction at 50 °C, the mixed solution was extracted with dichloromethane and water, the organic phases were combined, the organic solvent was concentrated, and the product was further purified by column chromatography to obtain 2-deuterated-4-hexyltoluene. The yield was 58%. Deuteration rate>98%. 1HNMR: δ7.21(t,J=6.0Hz,1H),7.03(d,J=9.0Hz,2H),2.61(t,J=6.0Hz,2H),2.98(s,3H),1.67~1.63 (m, 2H), 1.43~1.28 (s, 6H), 0.94 (t, J=9.0Hz, 3H). 13C NMR: δ142.80, 137.58, 128

[0039] Example 2: Preparation method of 2-deuterated-4-(2-ethyl-1,3-dioxolane)toluene

[0040] Palladium acetate (44.9 mg, 0.2 mmol), triphenylphosphine (52.4 mg, 0.2 mmol), sodium deuteroformate (276 mg, 4 mmol), norbornene (188 mg, 2 mmol), phosphoric acid were successively added to the 25 mL eggplant flask. Potassium (2.544g, 12mmol), potassium acetate (392mg, 4mmol), 2-iodotoluene (436mg, 2mmol), 2-(2-bromoethyl)-1,3-dioxane (1.448g, 8mmol) and Dimethylformamide (10ml). High-purity nitrogen was replaced three times, and after 16 hours of reaction at 50°C, the mixed solution was extracted with dichloromethane and water, the organic phases were combined, the organic solvent was concentrated, and the product was further purified by column chromatography to obtain 2-deuterated-4-(2-ethyl acetate) -1,3-dioxolane) toluene, yield 74%. Deuteration rate>98%. 1H NMR: δ7.18 (t, J=7.5Hz, 1H), 7.01 (dd, J=7.4, 3.0Hz, 2H), 4.91 (t, J=4.7Hz, 1H), 3.94 (m, 4H), 2.73(dd, J=9.5, 6.9Hz, 2H)

[0041] Embodiment 3: the preparation method of 2-deuterated-3-methylbenzene butyric acid ethyl ester

[0042] Palladium acetate (44.9 mg, 0.2 mmol), triphenylphosphine (52.4 mg, 0.2 mmol), sodium deuteroformate (276 mg, 4 mmol), norbornene (188 mg, 2 mmol), phosphoric acid were successively added to the 25 mL eggplant flask. Potassium (2.544 g, 12 mmol), potassium acetate (392 mg, 4 mmol), 2-iodotoluene (436 mg, 2 mmol), ethyl bromobutyrate (1.56 g, 8 mmol) and dimethylformamide (10 ml). High-purity nitrogen was replaced three times, and after 16 hours of reaction at 50 °C, the mixed solution was extracted with dichloromethane and water, the organic phases were combined, the organic solvent was concentrated, and the product was further purified by column chromatography to obtain 2-deuterated-3-methylphenylbutyric acid. Ethyl ester, yield 65%. Deuteration rate>98%. 1H NMR: δ7.17 (t, J=7.5Hz, 1H), 6.99 (t, J=7.7Hz, 2H), 4.13 (q, J=7.1Hz, 2H), 2.61 (t, J=7.6Hz, 2H), 2.32(m, 5H),