반응 #673310

반응 방정식

AlCl3

oxalyl chloride

5-bromo-2-chlorobenzoic acid

anisole

→

5-Bromo-2-chloro-4′-methoxybenzophenone

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타to removal of the volatiles
2. 2
   기타a rotary evaporator
3. 3
   workup.DISSOLUTIONAfter dissolving the crude 5-bromo-2-chlorobenzoyl chloride in 8 ml of CS2
4. 4
   온도the stirred mixture was cooled to 4°
5. 5
   기타The reaction
6. 6
   온도after warming to 20° over 1 hr
7. 7
   workup.STIRRINGwas stirred for 20 hr
8. 8
   기타to quenching with 1N HCl
9. 9
   workup.ADDITIONSubsequently, the suspension was diluted with 50 ml H2O
10. 10
    workup.STIRRINGstirred until all solids
11. 11
    추출The mixture was extracted 3× with EtOAc
12. 12
    세척The combined organic extracts were washed 1× with 1N HCl, H2O, aq NaHCO3, and brine
13. 13
    건조to drying over Na2SO4
14. 14
    기타After removal of the volatiles
15. 15
    기타the residue was chromatographed on silica gel using 15% EtOAc/hexane
16. 16
    세척to elute 450 mg of 5-bromo-2-chloro-4′-methoxybenzophenone

실험 절차

To a stirred suspension of commercial 5-bromo-2-chlorobenzoic acid (506 mg, 2.12 mmol) in 10 mL of CH2Cl2 containing oxalyl chloride (2.4 mmol) was added 2 drops of DMF. Once the vigorous evolution of gas ceased, the reaction was stirred 1.5 hr prior to removal of the volatiles using a rotary evaporator. After dissolving the crude 5-bromo-2-chlorobenzoyl chloride in 8 ml of CS2, the stirred mixture was cooled to 4° prior to adding anisole (240 mg, 2.12 mmol) followed by AlCl3 (566 mg, 4.25 mmol). The reaction, after warming to 20° over 1 hr, was stirred for 20 hr prior to quenching with 1N HCl. Subsequently, the suspension was diluted with 50 ml H2O and stirred until all solids were in solution. The mixture was extracted 3× with EtOAc. The combined organic extracts were washed 1× with 1N HCl, H2O, aq NaHCO3, and brine prior to drying over Na2SO4. After removal of the volatiles, the residue was chromatographed on silica gel using 15% EtOAc/hexane to elute 450 mg of 5-bromo-2-chloro-4′-methoxybenzophenone.

출처