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

HRID 1483187Notes

Reaction equation

HRID 1483187 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f27074e33f1641e48fc30f93b92ec310
Source dataset
uspto-grants-2016_08
Patent number
US09416121B2

Reaction notes

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