Reaktion #2487436

Reaktionsgleichung

4-(bromomethyl)-3-fluorobenzonitrile

thiourea

→

3-Fluoro-4-(mercaptomethyl)benzonitrile

Lösungsmittel

ethyl alcohol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux for 1 h
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   WaschenThe 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
   WaschenThe organic layer was washed with H2O (25 mL) and brine (25 mL)
8. 8
   Trocknendried over anhydrous Na2SO4
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    Sonstigeto afford the crude I-2 (300 mg)
11. 11
    SonstigeThe crude material was used without further purification

Vorschrift

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).

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