Methyl vinyl sulfone → HCID 86672573, compound

HRID 1475802Notes

Reaction equation

HRID 1475802 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7](I)=[C:6]([O:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[CH:5]=1.[CH:22]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH2:23].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(=O)OCC>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7](/[CH:23]=[CH:22]/[S:24]([CH3:27])(=[O:26])=[O:25])=[C:6]([O:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[CH:5]=1

Participants

8

Reactant 4

HCID 19354Methyl vinyl sulfoneHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 671709004-Iodo-3-(2-m-tolyl-ethoxy)-benzoic Acid Methyl Ester

Product 1

HCID 86672573HCID 86672573, compoundYield 57.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

500 mg of 4-Iodo-3-(2-m-tolyl-ethoxy)-benzoic acid methyl ester, 200 mg of methyl vinyl sulfone, 115 mg of tri-o-tolylphosphine, and 43 mg of palladium(II) acetate were stirred in 4 ml of acetonitrile and 1.5 ml of diisopropylethylamin for 2 h at 82° C. The reaction mixture was allowed to cool to room temperature. 10 ml of EA were then added and the mixture was washed successively twice using 5 ml of water each and twice using 5 ml of a saturated aqueous Na2CO3-solution. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:2 yielded 270 mg of the title compound. Rf (EA/HEP 1:2)=0.17

Workup

  1. washthe mixture was washed successively twice
  2. customThe organic layer was then dried
  3. customevaporated

Sources & evidence

ORD record
ord-6521d975731b4d4f91b9b841121de92a
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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