反应 #2487436

反应方程式

4-(bromomethyl)-3-fluorobenzonitrile

thiourea

→

3-Fluoro-4-(mercaptomethyl)benzonitrile

溶剂

ethyl alcohol

反应条件

后处理

1. 1
   温度was heated
2. 2
   温度to reflux for 1 h
3. 3
   浓缩concentrated under reduced pressure
4. 4
   洗涤The residue was washed with EtOAc (50 mL)
5. 5
   workup.ADDITIONtreated with 1.6 N NaOH
6. 6
   workup.ADDITIONdiluted with Et2O (50 mL)
7. 7
   洗涤The organic layer was washed with H2O (25 mL) and brine (25 mL)
8. 8
   干燥dried over anhydrous Na2SO4
9. 9
   浓缩concentrated under reduced pressure
10. 10
    其他to afford the crude I-2 (300 mg)
11. 11
    其他The crude material was used without further purification

实验过程

A mixture of 4-(bromomethyl)-3-fluorobenzonitrile (0.8 g, 3.7 mmol) and thiourea (0.57 g, 7.4 mmol) in ethyl alcohol (EtOH; 20 mL) was heated to reflux for 1 h. The progress of the reaction was monitored by TLC; the reaction mixture was cooled to RT and concentrated under reduced pressure. The residue was washed with EtOAc (50 mL), treated with 1.6 N NaOH and stirred for 20 h at RT. The reaction mixture was adjusted to pH˜4 with concentrated HCl and diluted with Et2O (50 mL). The organic layer was washed with H2O (25 mL) and brine (25 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude I-2 (300 mg). The crude material was used without further purification. 1H NMR (500 MHz, CDCl3): δ 7.45 (dd, J=9.5 Hz, 1.5 Hz, 1H), 7.40-7.37 (m, 2H), 3.76 (s, 2H).

来源