HCID 86617428, compound → HCID 86617427, compound

HRID 2076683Notes

Reaction equation

HRID 2076683 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:4]([C:13]#[CH:14])[CH:3]=1>CO.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[C:4]([CH2:13][CH3:14])[CH:3]=1

Participants

4

Reactant 1

HCID 86617428HCID 86617428, compound

Product 1

HCID 86617427HCID 86617427, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 887MethanolSolvent

Procedure

Chlorotris(triphenylphosphine)rhodium (65 mg, 69.9 μmol) was added to a solution of methyl (4-bromo-2-ethynylphenyl)acetate (177 mg, 0.699 mmol) obtained in Example (85-2) in methanol (6 ml), and the mixture was stirred at room temperature under hydrogen atmosphere for 16 hours. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=15/1) to give methyl (4-bromo-2-ethylphenyl)acetate (138 mg, yield: 77%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-19fef49ad95147dbae42363c7383f9e8
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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