反应 #1088

反应方程式

3-bromo-benzo[b]thiophene

4-benzyloxyphenol

→

benzo[b]thiophene

收率 28.0%

溶剂

collidine

ethyl acetate

反应条件

后处理

1. 1
   温度The mixture was heated
2. 2
   温度to reflux for 24 hours
3. 3
   温度Upon cooling
4. 4
   过滤the crude mixture filtered through a pad of Celite® (Aldrich, Milwaukee, Wis.)
5. 5
   其他to remove inorganic salts
6. 6
   洗涤The filtrate was washed with 1N hydrochloric acid (3×150 mL)
7. 7
   干燥The organic was dried (sodium sulfate)
8. 8
   浓缩concentrated in vacuo to a liquid
9. 9
   其他Thianaphthene was removed by distillation (10 mm Hg, 115°-120° C.)
10. 10
    其他The remainder of the material was chromatographed (silicon dioxide, hexanes: ethyl acetate 85:15)

实验过程

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.

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