تفاعل #1088

معادلة التفاعل

3-bromo-benzo[b]thiophene

4-benzyloxyphenol

→

benzo[b]thiophene

المردود 28.0%

المذيبات

collidine

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةto reflux for 24 hours
3. 3
   درجة الحرارةUpon cooling
4. 4
   ترشيحthe crude mixture filtered through a pad of Celite® (Aldrich, Milwaukee, Wis.)
5. 5
   أخرىto remove inorganic salts
6. 6
   غسيلThe filtrate was washed with 1N hydrochloric acid (3×150 mL)
7. 7
   تجفيفThe organic was dried (sodium sulfate)
8. 8
   تركيزconcentrated in vacuo to a liquid
9. 9
   أخرىThianaphthene was removed by distillation (10 mm Hg, 115°-120° C.)
10. 10
    أخرىThe remainder of the material was chromatographed (silicon dioxide, hexanes: ethyl acetate 85:15)

الإجراء التجريبي

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.

المصدر