반응 #48099

반응 방정식

oxalyl chloride

dimethylformamide

5-bromo-2-chloro-benzoic acid

→

(5-Bromo-2-chloro-phenyl)-(4-methoxy-phenyl)-methanone

용매

dichloromethane

반응 조건

후처리

1. 1
   여과filtered
2. 2
   기타separated from all volatile constituents in a rotary evaporator
3. 3
   workup.DISSOLUTIONThe residue is dissolved in 150 mL dichloromethane
4. 4
   workup.ADDITION46.5 g anisole are added
5. 5
   workup.ADDITIONThen 51.5 g aluminum trichloride are added batchwise so that the temperature
6. 6
   기타does not exceed 5° C
7. 7
   workup.STIRRINGThe solution is stirred for 1 h at 1 to 5° C.
8. 8
   workup.ADDITIONpoured
9. 9
   기타onto crushed ice
10. 10
    기타The organic phase is separated off
11. 11
    추출the aqueous phase is extracted with dichloromethane
12. 12
    세척The combined organic phases are washed with 1 M hydrochloric acid, twice with 1 M sodium hydroxide solution and with brine
13. 13
    건조Then the organic phase is dried over sodium sulfate
14. 14
    기타the solvent is removed
15. 15
    기타the residue is recrystallized from ethanol

실험 절차

38.3 mL oxalyl chloride and 0.8 mL dimethylformamide are added to a mixture of 100 g 5-bromo-2-chloro-benzoic acid in 500 mL dichloromethane. The reaction mixture is stirred for 14 h, then filtered and separated from all volatile constituents in a rotary evaporator. The residue is dissolved in 150 mL dichloromethane, the resultant solution is cooled to −5° C., and 46.5 g anisole are added. Then 51.5 g aluminum trichloride are added batchwise so that the temperature does not exceed 5° C. The solution is stirred for 1 h at 1 to 5° C. and then poured onto crushed ice. The organic phase is separated off, and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with 1 M hydrochloric acid, twice with 1 M sodium hydroxide solution and with brine. Then the organic phase is dried over sodium sulfate, the solvent is removed and the residue is recrystallized from ethanol.

출처