Reaction #2857

Reaction equation

5H-Thieno[3,2-c]pyridin-4-one

phosphorous oxy chloride

→

title compound

4-Chloro-thieno[3,2-c]pyridine

Conditions

Workup

1. 1
   Concentrationthe solution is concentrated
2. 2
   workup.DISSOLUTIONThe residue is dissolved in CH2 Cl2
3. 3
   WashThe resulting solution is washed with water and saturated NaCl
4. 4
   DryingThe organic layer is dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   OtherThe crude product is purified by column chromatography
8. 8
   Washeluting with a gradient of 40% CH2Cl2 /hexanes to 60% CH2Cl2 /hexanes

Procedure

5H-Thieno[3,2-c]pyridin-4-one (1.0 g, 6.62 mmol) is dissolved in 30 mL of phosphorous oxy chloride. The solution is heated to 100° C. After 4 h, the solution is concentrated. The residue is dissolved in CH2 Cl2. The resulting solution is washed with water and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 40% CH2Cl2 /hexanes to 60% CH2Cl2 /hexanes. The title compound (1.0 g, 5.8 mmol) is obtained as a white solid.

Source