HCID 89477928, compound → HCID 89477854, compound

HRID 1483195Notes

Reaction equation

HRID 1483195 reaction equation
[Br:1][C:2]1[C:22]([CH3:23])=[CH:21][C:5]([O:6][C:7](=[O:20])[C:8]#[C:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=1[CH3:24]>ClCCl.FC(F)(F)C(O)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[C:22]([CH3:23])=[C:21]2[C:5](=[CH:4][C:3]=1[CH3:24])[O:6][C:7](=[O:20])[CH:8]=[C:9]2[C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 1

HCID 89477928HCID 89477928, compound

Product 1

HCID 89477854HCID 89477854, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirring solution of methyl 3-(3-(4-bromo-3,5-dimethylphenoxy)-3-oxoprop-1-yn-1-yl)benzoate (9-3) (95 mg, 0.25 mmol) in dichloromethane (1 mL) and trifluoroacetic acid (2 mL) was added palladium acetate (5 mg, 0.02 mmol) under ice-cooling. After stirred for 3 h under ice-cooling, the mixture was diluted with 1,2-dichloromethane and evaporated to dryness. Chromatography of the residue on a silica gel (chloroform:hexanes=1:1-1:0) gave title compound 9-4 (69 mg, 73% yield) as a light brown gum.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-cea4a129510c4d228fd61892181ae57c
Source dataset
uspto-grants-2016_08
Patent number
US09416121B2

Reaction notes

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