Tributylvinyltin → 2-Benzoyl-4-(5-fluoro-2-vinylphenyl)-4-methylvaleric acid-methyl ester

HRID 1247564Notes

Reaction equation

HRID 1247564 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]([C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5][C:6]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1Br)([CH3:8])[CH3:7].[CH:26]([Sn](CCCC)(CCCC)CCCC)=[CH2:27]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3](=[O:25])[CH:4]([C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:5][C:6]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH:26]=[CH2:27])([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 695164952-Benzoyl-4-(2-bromo-5-fluorophenyl)-4-methylvaleric acid-methyl ester

Product 1

HCID 695176402-Benzoyl-4-(5-fluoro-2-vinylphenyl)-4-methylvaleric acid-methyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution of 0.53 g (1.25 mmol) of 2-benzoyl-4-(2-bromo-5-fluorophenyl)-4-methylvaleric acid-methyl ester and 77 mg (0.07 mmol) of tetrakis(triphenylphosphine)palladium in 40 ml of toluene is refluxed with vinyl(tributyl)stannane for 8 hours. Then, it is concentrated by evaporation and purified by column chromatography on silica gel with hexane-ethyl acetate: 320 mg of product.

Workup

  1. concentrationThen, it is concentrated by evaporation
  2. custompurified by column chromatography on silica gel with hexane-ethyl acetate

Sources & evidence

ORD record
ord-3d544d7df10d4e7a9a7d4254110142e3
Source dataset
uspto-grants-2006_10
Patent number
US07129270B2

Reaction notes

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