Reacción #1088

Ecuación de reacción

3-bromo-benzo[b]thiophene

4-benzyloxyphenol

→

benzo[b]thiophene

Rendimiento 28.0%

Disolventes

collidine

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturato reflux for 24 hours
3. 3
   TemperaturaUpon cooling
4. 4
   Filtraciónthe crude mixture filtered through a pad of Celite® (Aldrich, Milwaukee, Wis.)
5. 5
   Otroto remove inorganic salts
6. 6
   LavadoThe filtrate was washed with 1N hydrochloric acid (3×150 mL)
7. 7
   SecadoThe organic was dried (sodium sulfate)
8. 8
   Concentraciónconcentrated in vacuo to a liquid
9. 9
   OtroThianaphthene was removed by distillation (10 mm Hg, 115°-120° C.)
10. 10
    OtroThe remainder of the material was chromatographed (silicon dioxide, hexanes: ethyl acetate 85:15)

Procedimiento

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.

Fuente