Sodium Carbonate → 3-Methyl-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-phenylnaphthalene

HRID 1992821Notes

Reaction equation

HRID 1992821 reaction equation
Br[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[C:3]=1[O:15][CH2:16][O:17][CH3:18].[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:12][C:11]1[C:2]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:3]([O:15][CH2:16][O:17][CH3:18])[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([O:13][CH3:14])=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 685362562-Bromo-6-methoxy-1-(methoxymethoxy)-3-methylnaphthalene

Product 1

HCID 685363903-Methyl-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}-2-phenylnaphthaleneYield 182.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
160 °C

Procedure

2-Bromo-3-methyl-6-(methyloxy)-1-{[(methyloxy)methyl]oxy}naphthalene (14) (2.32 g, 7.46 mmol), phenylboronic acid (1.83 g, 15.0 mmol, 2.0 eq), tetrakistriphenylphosphine palladium (0) (0.869 g, 0.752 mmol, 10 mol %), 2 M sodium carbonate (65 mL), and ethylene glycol dimethyl ether (65 mL) were combined in a glass pressure bottle. The bottle was sealed with a screw cap and the reaction mixture was heated at 160° C. with stirring for 25 min. The reaction mixture was allowed to cool at RT. The reaction mixture was transferred to a separatory funnel and extracted with Et2O. The organic phase was separated, dried over MgSO4, filtered, and the filtrate was concentrated to give 4.96 g of the crude product. The crude product was combined with an additional 4.43 g of crude product (from a second Suzuki coupling reaction) and purified the crude product by chromatography over SiO2 with hexanes:CH2Cl2 (2:3) to give 4.2 g (91%) of the title compound (15) as a yellow oil. 1H NMR (400 MHz; DMSO-d6): δ 2.13 (s, 3H), 2.98 (s, 3H), 3.86 (s, 3H), 4.64 (s, 2H), 7.13 (dd, J=2.4 Hz, 9.1 Hz, 1H), 7.25 (d, J=2.4 Hz, 1H), 7.29 (d, J=7.0 Hz, 2H), 7.36 (t, J=7.5 Hz, 1H), 7.45 (t, J=7.5 Hz, 2H), 7.51 (s, 1H), 7.94 (d, J=9.1 Hz, 1H).

Workup

  1. customThe bottle was sealed with a screw
  2. customcap
  3. temperatureto cool at RT
  4. customThe reaction mixture was transferred to a separatory funnel
  5. extractionextracted with Et2O
  6. customThe organic phase was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customto give 4.96 g of the crude product
  11. customfrom a second Suzuki coupling reaction) and
  12. custompurified the crude product by chromatography over SiO2 with hexanes:CH2Cl2 (2:3)

Sources & evidence

ORD record
ord-b435d498a5764016b88f2bf1b17abea0
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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