4-溴-3-氟苯乙酸是重要的有机合成中间体,广泛应用于医药和农药领域的精细化学品合成。
医药; 农药
路线1:
- 原料:3-氟-4-溴苯基乙腈(153a,0.78 g,3.64 mmol)
- 步骤:将3-氟-4-溴苯基乙腈溶于硫酸(5 mL)和水(5 mL)的混合溶液中,于100℃下搅拌反应16小时。通过LCMS监测反应进程,确认原料完全消耗后,将反应混合物溶于水(20 mL)中,并用乙酸乙酯(20 mL)萃取。合并有机层,用无水硫酸钠干燥,过滤后减压浓缩,得到白色固体2-(4-溴-3-氟苯基)乙酸。
- 收率:56.1%(0.7 g,2.046 mmol)
- 表征:1H NMR(400 MHz,CD3OD)δ 7.53(t,J = 7.8 Hz,1H),7.16(dd,J = 9.8, 1.9 Hz,1H),7.02(d,J = 8.0 Hz,1H),3.61(s,2H)
- 参考文献:[1] Patent: WO2018/39386, 2018, A1. Location in patent: Page/Page column 302;[2] Patent: US2014/275111, 2014, A1. Location in patent: Paragraph 0349; 0350;[3] Patent: WO2014/141187, 2014, A1. Location in patent: Page/Page column 76;[4] Patent: WO2007/69986, 2007, A1. Location in patent: Page/Page column 92-93;[5] Patent: WO2017/98440, 2017, A1. Location in patent: Page/Page column 184
路线2:
- 原料:2-(4-溴-3-氟苯基)乙腈(153a,3.9 g,18.22 mmol)
- 步骤:向烧瓶中加入2-(4-溴-3-氟苯基)乙腈,Vater(3.75 mL),硫酸(3.75 mL)和AcOH(3.75 mL)。将得到的混合物在105℃下搅拌2小时。冷却至室温后,过滤收集固体,得到2-(4-溴-3-氟苯基)乙酸。
- 收率:95%(4.0 g,18.22 mmol)
- 参考文献:[1] Patent: WO2018/39386, 2018, A1. Location in patent: Page/Page column 302;[2] Patent: US2014/275111, 2014, A1. Location in patent: Paragraph 0349; 0350;[3] Patent: WO2014/141187, 2014, A1. Location in patent: Page/Page column 76;[4] Patent: WO2007/69986, 2007, A1. Location in patent: Page/Page column 92-93;[5] Patent: WO2017/98440, 2017, A1. Location in patent: Page/Page column 184