تفاعل #2487436

معادلة التفاعل

4-(bromomethyl)-3-fluorobenzonitrile

thiourea

→

3-Fluoro-4-(mercaptomethyl)benzonitrile

المذيبات

ethyl alcohol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةto reflux for 1 h
3. 3
   تركيزconcentrated under reduced pressure
4. 4
   غسيلThe 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
   غسيلThe organic layer was washed with H2O (25 mL) and brine (25 mL)
8. 8
   تجفيفdried over anhydrous Na2SO4
9. 9
   تركيزconcentrated under reduced pressure
10. 10
    أخرىto afford the crude I-2 (300 mg)
11. 11
    أخرىThe crude material was used without further purification

الإجراء التجريبي

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).

المصدر