反应详情

温度

36 °C

Add 2-(4-iodophenyl)benzoic acid (12.0 grams, 0.037 moles, preparation 55), dichloromethane (60 mL), dimethylformamide (0.5 mL, 0.0065 moles), and thionyl chloride (5.72 grams, 0.0481 moles) to a 250 mL 3-neck round-bottom flask equipped with a magnetic stirrer, internal temperature probe, heating mantle, condenser, and nitrogen inlet. Warm the reaction mixture to 36° C. for 45 minutes. Add thionyl chloride (1.7 grams, 0.0143 moles) and stir at 36° C. for 15 minutes. Add tetrahydrofuran (60 mL) dichloromethane (60 mL) and concentrated ammonium hydroxide (25 mL, 0.37 moles) to a 500 mL 3-neck round-bottom flask equipped with a magnetic stirrer, internal temperature probe, and cooling bath. Add the contents of the 250 mL flask to the 500 mL flask over 5 minutes while limiting the temperature to 30° C. Cool the reaction mixture to 18° C. and filter to collect the precipitate. Retain the filter cake. Transfer the filtrate to a separatory funnel and separate the phases. Concentrate the organic phase under reduced pressure (15-25 mm) to a solid, and suspend the solid in methyl-tert-butyl ether (25 mL). Isolate the solid by filtration and combine with the retained filter cake from above. Suspend the combined solids in methyl-tert-butyl ether (40 mL) at ambient temperature. Filter to isolate the solids. Suspend the solids in 50 mL water, and filter to recover the solids. Rinse the filter cake twice with water (20 mL). Dry the solids at 40° C. under reduced pressure (15-25 mm) to provide the title compound (9.7 grams, 0.030 moles, 81.1% yield). 1H NMR (acetone-d6, 500.0 MHz): δ 7.82 (d, 2H), J=8.8; 7.58 (d, 1H, J=8.2); 7.54 (td, 1H), J=7.7, 1.6; 7.46 (td, 1H, J=7.7, 1.1); 7.42 (d, 1H, J=7.6); 7.30 (d, 2H, J=8.8); 6.91 (s, 1H); 6.62 (s, 1H).

1. customequipped with a magnetic stirrer
2. temperatureinternal temperature probe, heating mantle, condenser, and nitrogen inlet
3. temperatureinternal temperature probe, and cooling bath
4. additionAdd the contents of the 250 mL flask to the 500 mL flask over 5 minutes
5. customto 30° C
6. temperatureCool the reaction mixture to 18° C.
7. filtrationfilter
8. customto collect the precipitate
9. customseparate the phases
10. concentrationConcentrate the organic phase under reduced pressure (15-25 mm) to a solid
11. customIsolate the solid
12. filtrationby filtration
13. filtrationretained filter cake from above
14. customat ambient temperature
15. filtrationFilter
16. customto isolate the solids
17. filtrationfilter
18. customto recover the solids
19. washRinse the filter cake twice with water (20 mL)
20. customDry the solids at 40° C. under reduced pressure (15-25 mm)