Potassium Carbonate → 2-Methoxy-6-(3-methoxyphenyl)naphthalene

HRID 1943536Notes

Reaction equation

HRID 1943536 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[C:14](=[O:17])([O-])[O-].[K+].[K+]>[Pd].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(O)C.O>[CH3:13][O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:2]3[CH:11]=[CH:10][CH:9]=[C:4]([O:17][CH3:14])[CH:3]=3)[CH:3]=2)[CH:8]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 787862-Bromo-6-methoxynaphthalene

Product 1

HCID 114028342-Methoxy-6-(3-methoxyphenyl)naphthaleneYield 188.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of a mixed solvent (toluene/ethanol/water=2.5/2.5/1; 500 ml), the compound (T-2) (48.6 g, 319.6 mmol), 2-bromo-6-methoxynaphthalene (42.9 g, 181.0 mmol), 5% palladium on carbon (2.15 g), potassium carbonate (37.5 g, 271.5 mmol) and tetrabutylammonium bromide (14.6 g, 45.3 mmol) was refluxed with stirring for 15 hours under an atmosphere of nitrogen. The resulting reaction mixture was extracted with toluene (300 mL) three times, and the organic layer was washed with water. After the organic layer had been dried over anhydrous magnesium sulfate, the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: toluene), and then by recrystallization from a mixed solvent of heptane, methanol and ethyl acetate to give colorless crystals (45.0 g) of 2-methoxy-6-(3-methoxyphenyl)naphthalene (T-9).

Workup

  1. customThe resulting reaction mixture
  2. extractionwas extracted with toluene (300 mL) three times
  3. washthe organic layer was washed with water
  4. dry with materialAfter the organic layer had been dried over anhydrous magnesium sulfate
  5. distillationthe organic solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography (eluent: toluene)
  7. customby recrystallization from a mixed solvent of heptane, methanol and ethyl acetate

Sources & evidence

ORD record
ord-93e21f48d24d4f0bbee4c12bf060d6bb
Source dataset
uspto-grants-2013_03
Patent number
US08394468B2

Reaction notes

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