1,3-Dibromobenzene → HCID 57475766, 화합물

n-Butyllithium (2.64 M, 37.9 mL) was added dropwise to a solution of 1,3-dibromobenzene (23.5 g) in tetrahydrofuran (469 mL) at −78° C. The mixture was stirred at the same temperature for 30 minutes, and then tetrahydro-4H-pyran-4-one (10.0 g) was added dropwise. The mixture was stirred at the same temperature for 30 minutes and then warmed to room temperature. After stirring at room temperature for four hours, an ammonium chloride solution was added to the reaction mixture to terminate the reaction. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was dissolved in toluene (400 mL). p-Toluenesulfonic acid monohydrate (2 g) was added and the mixture was stirred with heating under reflux for two hours. The reaction mixture was cooled to room temperature and purified by NH-silica gel column chromatography to obtain the title compound (21.4 g).

1. stirringThe mixture was stirred at the same temperature for 30 minutes
2. stirringAfter stirring at room temperature for four hours
3. customto terminate
4. customthe reaction
5. extractionThe aqueous layer was extracted with ethyl acetate
6. washthe organic layer was washed with water and brine
7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
8. customThe solvent was evaporated under reduced pressure
9. dissolutionthe resulting residue was dissolved in toluene (400 mL)
10. additionp-Toluenesulfonic acid monohydrate (2 g) was added
11. stirringthe mixture was stirred
12. temperaturewith heating
13. temperatureunder reflux for two hours
14. temperatureThe reaction mixture was cooled to room temperature
15. custompurified by NH-silica gel column chromatography

ORD 기록

ord-bc23ddbecbd243aa84082da2e95e3260

출처 데이터셋

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08946211B2