Réaction #955900

Équation de réaction

4-hydroxythiophenol

2-bromoethanol

K2CO3

→

(a)

Rendement 72.0%

Solvants

dimethylformamide

—

ice water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with dichloromethane (DCM) (3×50 ml)
2. 2
   SéchageThe organic part was dried by MgSO4
3. 3
   Autresolvent was removed under a rotary evaporator
4. 4
   AutreThe crude product was purified on silica gel column

Mode opératoire

(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).

Source