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1,2-Dichloroethane → N-[2-bromo-4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl]phenylmethyl]phthalimide

HRID 2386156
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HRID 2386156 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:24])[CH:10]=[C:11]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][C:7]=1[CH3:8].Br[N:26]1[C:30](=[O:31])[CH2:29][CH2:28][C:27]1=[O:32].N([C:40]([CH3:44])([CH3:43])C#N)=NC(C)(C)C#N.O.Cl[CH2:47]CCl>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:24])[CH:10]=[C:11]([C:16]2[CH:17]=[C:18]([Cl:23])[CH:19]=[C:20]([Cl:22])[CH:21]=2)[C:12]([F:14])([F:15])[F:13])[CH:5]=[CH:6][C:7]=1[CH2:8][N:26]1[C:30](=[O:31])[C:29]2=[CH:47][CH:44]=[CH:40][CH:43]=[C:28]2[C:27]1=[O:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 6547Azobisisobutyronitrile2회HCID 67184N-bromobutanimide2회HCID 866480681-(3-Bromo-4-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butene-1-one

생성물 1

HCID 86648069
N-[2-bromo-4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl]phenylmethyl]phthalimide

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 2.00 g of 1-(3-bromo-4-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butene-1-one in 15 mL of 1,2-dichloroethane, 0.98 g of N-bromosuccinimide and 0.06 g of α,α′-azobisisobutyronitrile were added, and the resultant reaction mixture was stirred while heating the reaction mixture to reflux for 1 hour. Next, to the reaction mixture, 0.61 g of N-bromosuccinimide and 0.05 g of α,α′-azobisisobutyronitrile were added and the reaction mixture was continued to be stirred at the same temperature further for 2 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and was diluted with 50 mL of chloroform. Subsequently, the diluted reaction mixture was washed with water (30 mL×2) and then dehydrated and dried over a saturated brine and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The resultant residue was dissolved in 10 mL of N,N-dimethylformamide, and 0.85 g of phthalimide potassium was added to the resultant solution, followed by stirring the resultant reaction mixture at room temperature for 13 hours. After the completion of the reaction, 30 mL of water was added to the reaction mixture and the resultant reaction mixture was extracted with ethyl acetate (50 mL×1). The organic phase was dehydrated and dried over a saturated brine and anhydrous magnesium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 1.67 g of the objective substance as a yellow crystal.

후처리

  1. customthe resultant reaction mixture
  2. temperaturewhile heating the reaction mixture
  3. temperatureto reflux for 1 hour
  4. stirringto be stirred at the same temperature further for 2 hours
  5. customAfter the completion of the reaction
  6. waitthe reaction mixture was left
  7. customSubsequently, the diluted reaction mixture
  8. washwas washed with water (30 mL×2)
  9. dry with materialdried over a saturated brine and anhydrous sodium sulfate in this order
  10. distillationthe solvent was distilled off under reduced pressure
  11. dissolutionThe resultant residue was dissolved in 10 mL of N,N-dimethylformamide
  12. addition0.85 g of phthalimide potassium was added to the resultant solution
  13. stirringby stirring the resultant
  14. customreaction mixture at room temperature for 13 hours
  15. additionwas added to the reaction mixture
  16. customthe resultant reaction mixture
  17. extractionwas extracted with ethyl acetate (50 mL×1)
  18. dry with materialdried over a saturated brine and anhydrous magnesium sulfate in this order
  19. distillationthe solvent was distilled off under reduced pressure
  20. customThe resultant residue was purified by silica gel column chromatography
  21. washeluting with ethyl acetate-hexane (1:1)
  22. customto obtain 1.67 g of the objective substance as a yellow crystal

출처 및 근거

ORD 기록
ord-483ac413729e42caad37dce089e5f2d5
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08268754B2

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