반응 #1088

반응 방정식

3-bromo-benzo[b]thiophene

4-benzyloxyphenol

→

benzo[b]thiophene

수율 28.0%

용매

collidine

ethyl acetate

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도to reflux for 24 hours
3. 3
   온도Upon cooling
4. 4
   여과the crude mixture filtered through a pad of Celite® (Aldrich, Milwaukee, Wis.)
5. 5
   기타to remove inorganic salts
6. 6
   세척The filtrate was washed with 1N hydrochloric acid (3×150 mL)
7. 7
   건조The organic was dried (sodium sulfate)
8. 8
   농축concentrated in vacuo to a liquid
9. 9
   기타Thianaphthene was removed by distillation (10 mm Hg, 115°-120° C.)
10. 10
    기타The remainder of the material was chromatographed (silicon dioxide, hexanes: ethyl acetate 85:15)

실험 절차

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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