反応 #1088

反応方程式

3-bromo-benzo[b]thiophene

4-benzyloxyphenol

→

benzo[b]thiophene

収率 28.0%

溶媒

collidine

ethyl acetate

反応条件

後処理

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
   ろ過the crude mixture filtered through a pad of Celite® (Aldrich, Milwaukee, Wis.)
5. 5
   その他to remove inorganic salts
6. 6
   洗浄The filtrate was washed with 1N hydrochloric acid (3×150 mL)
7. 7
   乾燥The organic was dried (sodium sulfate)
8. 8
   濃縮concentrated in vacuo to a liquid
9. 9
   その他Thianaphthene was removed by distillation (10 mm Hg, 115°-120° C.)
10. 10
    その他The remainder of the material was chromatographed (silicon dioxide, hexanes: ethyl acetate 85:15)

実験手順

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.

出典