Reacción #2487436

Ecuación de reacción

4-(bromomethyl)-3-fluorobenzonitrile

thiourea

→

3-Fluoro-4-(mercaptomethyl)benzonitrile

Disolventes

ethyl alcohol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturato reflux for 1 h
3. 3
   Concentraciónconcentrated under reduced pressure
4. 4
   LavadoThe 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
   LavadoThe organic layer was washed with H2O (25 mL) and brine (25 mL)
8. 8
   Secadodried over anhydrous Na2SO4
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    Otroto afford the crude I-2 (300 mg)
11. 11
    OtroThe crude material was used without further purification

Procedimiento

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).

Fuente