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

HRID 1483187ノート

反応式

HRID 1483187 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f27074e33f1641e48fc30f93b92ec310
出典データセット
uspto-grants-2016_08
特許番号
US09416121B2

反応ノート

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