Reacción #417894

Ecuación de reacción

4-hydroxythiophenol

2-bromoethanol

K2CO3

→

(a)

Rendimiento 72.0%

Disolventes

dimethylformamide

—

ice water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with dichloromethane (DCM) (3×50 ml)
2. 2
   SecadoThe organic part was dried by MgSO4
3. 3
   Otrosolvent was removed under a rotary evaporator
4. 4
   OtroThe crude product was purified on silica gel column

Procedimiento

(FIG. 2) (a) (4-(2-hydroxyethylsulfanyl) phenol) was synthesized by a modified literature procedure (pl add ref). 4-hydroxythiophenol (mercaptophenol) (6.00 g, 47.61 mmole), 2-bromoethanol (5.90 g, 47.6 mmol) and K2CO3 (6.6 g, 47.48 mmol) was stirred in dimethylformamide (DMF, 50 ml) at −5° C. for 30 minutes. The reaction mixture was then stirred for 12 hours at room temperature. The reaction mixture was poured in ice water (300 ml) and extracted with dichloromethane (DCM) (3×50 ml). The organic part was dried by MgSO4 and then solvent was removed under a rotary evaporator. The crude product was purified on silica gel column by using a chloroform/methanol (94:6) solvent mixture. Yield: 72%. 1H NMR (CDCl3): δ, 8.01 (s, OH, 1H), 7.33 (d, 2H, J=8.7 Hz), 6.78 (d, 2H, J=8.7 Hz), 4.52 (s, OH, 1H), 3.67 (t, 2H, J=6 Hz), 2.99 (t, 2H, J=5.7).

Fuente