반응 #2193591

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 the rotary evaporator
3. 3
   workup.DISSOLUTIONThe residue is dissolved in 150 ml dichloromethane
4. 4
   workup.ADDITION46.5 g of anisole are added
5. 5
   workup.ADDITIONThen 51.5 g of aluminium trichloride are added batchwise so that the temperature
6. 6
   기타does not exceed 5° C
7. 7
   workup.STIRRINGThe solution is stirred for another 1 h at 1-5° C.
8. 8
   workup.ADDITIONpoured onto ice
9. 9
   기타The organic phase is separated off
10. 10
    추출the aqueous phase is extracted another three times with dichloromethane
11. 11
    세척The combined organic phases are washed with aqueous 1 M hydrochloric acid, twice with 1 M sodium hydroxide solution and with saturated sodium chloride solution
12. 12
    기타Then the organic phase is dried
13. 13
    기타the solvent is removed
14. 14
    기타the residue is recrystallised in ethanol

실험 절차

38.3 ml oxalyl chloride and 0.8 ml of dimethylformamide are added to a mixture of 100 g of 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 the rotary evaporator. The residue is dissolved in 150 ml dichloromethane, the solution is cooled to −5° C., and 46.5 g of anisole are added. Then 51.5 g of aluminium trichloride are added batchwise so that the temperature does not exceed 5° C. The solution is stirred for another 1 h at 1-5° C. and then poured onto ice. The organic phase is separated off and the aqueous phase is extracted another three times with dichloromethane. The combined organic phases are washed with aqueous 1 M hydrochloric acid, twice with 1 M sodium hydroxide solution and with saturated sodium chloride solution. Then the organic phase is dried, the solvent is removed and the residue is recrystallised in ethanol.

출처