反应详情

Cs2CO3 (1629 mg, 5 mmol) was added in one portion to a solution of 4-aminophenol (541 mg, 5 mmol) in acetonitrile (20 mL). The reaction mixture was stirred at room temperature for 30 min and cooled to 0° C. prior to the addition of a solution of bromoacetonitrile (313 μL, 5 mmol) in acetonitrile (10 mL) dropwise. After stirring at room temperature for 48 h (TLC control), the reaction mixture is filtered and the filtrate evaporated to dryness in vacuo. The residue obtained after solvent removal was purified by silica gel column chromatography (hexanes/EtOAc 1:1). The desired product was isolated as yellow-brown oil. Yield: 559 mg, 76%. TLC Rf=0.2 (hexanes/EtOAc 1:1). 1H NMR (CDCl3, 600 MHz): δ 3.56 (br.s, 2H, NH2), 4.66 (s, 2H, CH2), 6.65 (d, J=8.4 Hz, 2H), 6.83 (d, J=8.4 Hz, 2H). 13C NMR (CDCl3, 150 MHz): δ 55.28, 115.60, 116.25, 117.10, 142.42, 149.65. HRMS: Calcd. [M+H]+ m/z 149.0715, Observed 149.0689.

1. temperaturecooled to 0° C.
2. stirringAfter stirring at room temperature for 48 h (TLC control)
3. filtrationthe reaction mixture is filtered
4. customthe filtrate evaporated to dryness in vacuo
5. customThe residue obtained
6. customafter solvent removal
7. customwas purified by silica gel column chromatography (hexanes/EtOAc 1:1)