Thionyl Chloride → 1-Indanone, 4-bromo-

Thionyl chloride (85 ml) was added to 3-(2-bromophenyl)propionic acid (16.88 g), and the mixture was stirred under reflux for 2 hours. After the mixture was left standing for cooling, the excessive amount of the thionyl chloride was removed by distillation under reduced pressure, and the residual mixture was distilled azeotropically once with toluene and once with carbon tetrachloride. The residual concentrate was dissolved in carbon tetrachloride (30 ml) and added at a temperature of 5°-10° C. dropwise to a suspension of aluminum chloride (14.74 g) in carbon tetrachloride (100 ml). The mixture was stirred at the same temperature for 40 minutes, then at room temperature for 30 minutes and further under reflux for 1 hour. After left standing for cooling, the mixture was poured into ice-hydrochloric acid, and extracted with methylene chloride. The organic layer was washed with dilute hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous saline, and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residual concentrate was purified by chromatography on a silica gel column to give the title compound (13.2 g).

1. temperatureunder reflux for 2 hours
2. waitAfter the mixture was left
3. temperaturefor cooling
4. customthe excessive amount of the thionyl chloride was removed by distillation under reduced pressure
5. distillationthe residual mixture was distilled azeotropically once with toluene and once with carbon tetrachloride
6. concentrationThe residual concentrate
7. dissolutionwas dissolved in carbon tetrachloride (30 ml)
8. additionadded at a temperature of 5°-10° C. dropwise to a suspension of aluminum chloride (14.74 g) in carbon tetrachloride (100 ml)
9. stirringThe mixture was stirred at the same temperature for 40 minutes
10. temperaturefurther under reflux for 1 hour
11. waitAfter left standing
12. temperaturefor cooling
13. additionthe mixture was poured into ice-hydrochloric acid
14. extractionextracted with methylene chloride
15. washThe organic layer was washed with dilute hydrochloric acid
16. dry with materiala saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous saline, and dried over sodium sulfate
17. customThe solvent was removed by distillation under reduced pressure
18. concentrationthe residual concentrate
19. customwas purified by chromatography on a silica gel column

ORDレコード

ord-d2dd5b0f3a7e40c6b7914f90eb256663

出典データセット

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05594081