Реакция #955900

Уравнение реакции

4-hydroxythiophenol

2-bromoethanol

K2CO3

→

(a)

Выход 72.0%

Растворители

dimethylformamide

—

ice water

Условия реакции

Обработка

1. 1
   Экстракцияextracted with dichloromethane (DCM) (3×50 ml)
2. 2
   СушкаThe organic part was dried by MgSO4
3. 3
   Другоеsolvent was removed under a rotary evaporator
4. 4
   ДругоеThe crude product was purified on silica gel column

Методика

(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).

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