Potassium Carbonate → 2-Vinyl-6-methoxynaphthalene

HRID 857839Notes

Reaction equation

HRID 857839 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](Br)[CH:7]=[CH:6]2.C(=O)([O-])[O-].[K+].[K+].[CH2:20](P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)[CH2:21]CC>CN1C(=O)CCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:20]=[CH2:21])[CH:7]=[CH:6]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 787862-Bromo-6-methoxynaphthaleneHCID 11371790Bis(adamantan-1-yl)(butyl)phosphane

Product 1

HCID 6035352-Vinyl-6-methoxynaphthaleneYield 92%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

50 mmol of 6-methoxy-2-bromonaphthalene and 60 mmol of potassium carbonate are dissolved in 40 ml of NMP, and 0.001 mol % of Pd(OAc)2 and 0.004 mol % of butyldiadamantyl-phosphine are added. The mixture is placed under an ethylene pressure of 20 bar and stirred at 130° C. until conversion is complete. After filtration of the insoluble constituents, washing with alkaline solution and distillation, 92% of 6-methoxy-2-vinylnaphthalene is obtained.

Workup

  1. filtrationAfter filtration of the insoluble constituents
  2. washwashing with alkaline solution and distillation

Sources & evidence

ORD record
ord-d3638d5943ea41d8a330bbc21ef989fc
Source dataset
uspto-grants-2006_12
Patent number
US07148176B2

Reaction notes

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