Isopropenyl acetate → HCID 14368623, compound

HRID 1653835Notes

Reaction equation

HRID 1653835 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O:18][C:19]([CH3:21])=[CH2:20])(=O)C.C[O-].C([Sn+](CCCC)CCCC)CCC>C1(C)C=CC=CC=1.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH2:20][C:19](=[O:18])[CH3:21])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 7916Isopropenyl acetateHCID 27568764-Bromo-4'-chlorobiphenylHCID 11964040Methoxytri-n-butylstannane

Product 1

HCID 14368623HCID 14368623, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 178424406HCID 178424406, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of 4-bromo-4'-chlorobiphenyl (16 g; F. R. Shaw and E. E. Turner. J. Chem. Soc., 285 (1932) ), isopropenyl acetate (9 g) and dichlorobis(tri-o-tolylphosphine)palladium (0.47 g) in dry toluene (30 ml), under nitrogen, was added tributyltin methoxide (25.9 ml; Aldrich). The mixture was stirred and heated at 100° for 5 hr, cooled and the solvent evaporated in vacuo. The residue was chromatographed on silica gel, eluting with cyclohexane then ether. The resultant solid was recrystallised from cyclohexane to afford the title compound (10 g), m.p. 79°-81°.

Workup

  1. temperatureheated at 100° for 5 hr
  2. temperaturecooled
  3. customthe solvent evaporated in vacuo
  4. customThe residue was chromatographed on silica gel
  5. washeluting with cyclohexane
  6. customThe resultant solid was recrystallised from cyclohexane

Sources & evidence

ORD record
ord-e9b9488455b64804a38a0559ad86553b
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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