1,2-Dichloroethane → 6-Bromo-5,7-dimethyl-4-(3-nitrophenyl)-2H-chromen-2-one

HRID 1483187노트

반응식

HRID 1483187 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]#[C:11][C:12]([O:14][C:15]2[CH:20]=[C:19]([CH3:21])[C:18]([Br:22])=[C:17]([CH3:23])[CH:16]=2)=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(O)(C(F)(F)F)=O.ClCCCl>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:22][C:18]1[C:19]([CH3:21])=[C:20]2[C:15](=[CH:16][C:17]=1[CH3:23])[O:14][C:12](=[O:13])[CH:11]=[C:10]2[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

참가 물질

6

반응물 3

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 894777654-Bromo-3,5-dimethylphenyl 3-(3-nitrophenyl)propiolate

생성물 1

HCID 894780386-Bromo-5,7-dimethyl-4-(3-nitrophenyl)-2H-chromen-2-one수율 97.2%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 4-bromo-3,5-dimethylphenyl 3-(3-nitrophenyl)propiolate (6-2) (15.96 g, 42.65 mmol) in CH2Cl2 (100 mL) was added TFA (10 mL) and Pd(OAc)2 (480 mg, 2.14 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 4.5 h. To the mixture was added 1,2-dichloroethane and concentrated. Then toluene was added and concentrated. To the concentrate added toluene, dichloromethane and hexane, and the precipitated solid was collected by filtration. The solid was washed with hexane and dried to give the title compound 6-3 (15.51 g, 97% yield) as a brown solid.

후처리

  1. concentrationconcentrated
  2. additionThen toluene was added
  3. concentrationconcentrated
  4. additionTo the concentrate added toluene, dichloromethane and hexane
  5. filtrationthe precipitated solid was collected by filtration
  6. washThe solid was washed with hexane
  7. customdried

출처 및 근거

ORD 기록
ord-f27074e33f1641e48fc30f93b92ec310
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416121B2

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