反应详情

A 250 mL, 3 neck, round bottomed flask fitted with a mechanical agitator and connected to a sodium hydroxide scrubber is purged with nitrogen and charged with 2-(4-methoxyphenyl)-6-methoxybenzo[b]thiophene (5.3 g, 19.6 mmol), p-anisoyl chloride (3.68 g, 21.56 mmol), and 100 mL of methylene chloride. To this slurry at 20° C. is added boron trichloride (3.4 mL, 39.8 mmol) which had been condensed in a graduated cylinder. The reaction mixture is quenched after 40 minutes by the slow addition of 50 mL of methanol over approximately 5 minutes followed by addition of 50 mL of water over 5 minutes. The organic phase is washed with 50 mL brine, dried over sodium sulfate, filtered, and concentrated affording a dark orange oil. Addition of 10 mL of methanol followed by sonication for 5 minutes resulted in crystallization of 7.1 g of crude product as a yellow solid. The crude material is recrystallized from 3:1 hexanes/toluene affording 5.9 g of product as pale yellow crystals. (75%).

1. customA 250 mL, 3 neck, round bottomed flask fitted with a mechanical agitator
2. customis purged with nitrogen
3. customcondensed in a graduated cylinder
4. customThe reaction mixture is quenched after 40 minutes by the slow addition of 50 mL of methanol over approximately 5 minutes
5. additionfollowed by addition of 50 mL of water over 5 minutes
6. washThe organic phase is washed with 50 mL brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customaffording a dark orange oil
11. customfollowed by sonication for 5 minutes