Реакция #1088

Уравнение реакции

3-bromo-benzo[b]thiophene

4-benzyloxyphenol

→

benzo[b]thiophene

Выход 28.0%

Растворители

collidine

ethyl acetate

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Температураto reflux for 24 hours
3. 3
   ТемператураUpon cooling
4. 4
   Фильтрацияthe crude mixture filtered through a pad of Celite® (Aldrich, Milwaukee, Wis.)
5. 5
   Другоеto remove inorganic salts
6. 6
   ПромывкаThe filtrate was washed with 1N hydrochloric acid (3×150 mL)
7. 7
   СушкаThe organic was dried (sodium sulfate)
8. 8
   Концентрированиеconcentrated in vacuo to a liquid
9. 9
   ДругоеThianaphthene was removed by distillation (10 mm Hg, 115°-120° C.)
10. 10
    ДругоеThe remainder of the material was chromatographed (silicon dioxide, hexanes: ethyl acetate 85:15)

Методика

To a solution of 3-bromo-benzo[b]thiophene (69.62 g, 0.325 mol) in 55 mL of anhydrous collidine under N2 was added 4-benzyloxyphenol (97.6 g, 0.488 mol) and cuprous oxide (23.3 g, 0.163 mol). The mixture was heated to reflux for 24 hours. Upon cooling, the reaction mixture was diluted with ethyl acetate (200 mL) and the crude mixture filtered through a pad of Celite® (Aldrich, Milwaukee, Wis.) to remove inorganic salts. The filtrate was washed with 1N hydrochloric acid (3×150 mL). The organic was dried (sodium sulfate) and concentrated in vacuo to a liquid. Thianaphthene was removed by distillation (10 mm Hg, 115°-120° C.). The remainder of the material was chromatographed (silicon dioxide, hexanes: ethyl acetate 85:15) to provide 12.2 g of benzo[b]thiophene and 12.95 g (35% based on recovered starting material) of [3-(4-benzyloxy)phenoxy]benzo-[b]thiophene as an off-white solid. mp 84°-86° C. 1H NMR (CDCl3) d 7.91-7.83 (m, 2H), 7.47-7.34 (m, 7H), 7.04 (q, JAB =9.0 Hz, 4H), 6.47 (s, 1H), 5.07 (s, 2H). Anal. Calcd. for C21H16O2S: C, 75.88; H, 4.85. Found: C, 75.75; H, 5.00.

Источник