2-Naphthalenecarboxylic acid, 1-bromo-, methyl ester → HCID 68846043, compound

HRID 1889285Notes

Reaction equation

HRID 1889285 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1Br)=[O:4]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[CH:11]=[CH:10][CH2:9][CH2:8][C:7]1[CH:12]=[CH:13][CH:14]=[CH:5][CH:6]=1)=[O:4]

Participants

3

Reactant 1

HCID 109453332-Naphthalenecarboxylic acid, 1-bromo-, methyl ester

Product 1

HCID 68846043HCID 68846043, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

530 mg g 1-bromo-naphthalene-2-carboxylic acid methyl ester and 9 mg tris(dibenzylideneacetone)dipalladium(0) were placed in a reaction vial, which was evacuated and backfilled with argon three times. Via septum 125 μl tri-tert.butylphosphine (10% in hexane), 291 mg 4-phenyl-1-butene, 470 μl N,N-dicyclohexylmethylamine and 1.8 ml dioxane were added. After 2 h at 80° C., the reaction mixture was cooled and filtrated over silica with diethyl ether. After concentration of the organic phase the resulting residue was purified by chromatography on silica (ethyl acetate/heptane) to yield 175 mg of a mixture of the (E)- and (Z)-isomers of 1-(4-phenyl-but-1-enyl)-naphthalene-2-carboxylic acid methyl ester.

Workup

  1. customwere placed in a reaction vial
  2. customwhich was evacuated
  3. additionVia septum 125 μl tri-tert.butylphosphine (10% in hexane), 291 mg 4-phenyl-1-butene, 470 μl N,N-dicyclohexylmethylamine and 1.8 ml dioxane were added
  4. temperaturethe reaction mixture was cooled
  5. filtrationfiltrated over silica with diethyl ether
  6. customAfter concentration of the organic phase the resulting residue was purified by chromatography on silica (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-a509976b76ea4396a88b53242860ad7f
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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