HRID1591945

反应详情

EQUATION

反应方程式

HRID 1591945 的结构方程式

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

A mixture of 3,5-dibromo-4-pyridone (VIII, W=Br) (79.0 g, 0.312 mol) and PCl5 (79 g, 0.38 mol) was kept at 160° C. for 3 h. The reaction mixture was cooled to 0° C. and quenched by slow addition of water (200 mL). The resulting precipitate was crushed, filtered off, washed with water, and transferred on top of a flash silica column which was subsequently eluted with CH2Cl2. The crude product thus obtained was crystallised from EtOH to give the title compound, 3,5-dibromo-4-chloropyridine (VII, W=Br) (73.9 g, 72%) as white needles: Rf=0.60 (CH2Cl2); mp 95.0-96.5° C. (EtOH); 1H NMR (250 MHz, CDCl3) δ8.65 (s); 13C NMR (63 MHz, CDCl3) δ121.8, 144.0, and 150.9; IR (CHCl3) νmax 1549, 1524, 1410, and 1394 cm−1; MS (EI+) m/z (rel intensity) 271 (100%, M+) and 192 (30); HRMS calcd for C5H2Br2ClN (M+) 268.8242. found 268.8231.

WORKUP

后处理

  1. customquenched by slow addition of water (200 mL)
  2. customThe resulting precipitate was crushed
  3. filtrationfiltered off
  4. washwashed with water
  5. washwas subsequently eluted with CH2Cl2
  6. customThe crude product thus obtained
  7. customwas crystallised from EtOH