Sodium Carbonate → 2-Methoxy-6-(4-methoxyphenyl)naphthalene

HRID 858331Notes

Reaction equation

HRID 858331 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.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)CC>[CH3:13][O:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:19]3[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)[CH:3]=2)[CH:8]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 787862-Bromo-6-methoxynaphthaleneHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 111497342-Methoxy-6-(4-methoxyphenyl)naphthalene

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 10311-PropanolSolvent

Procedure

In an 100 mL three-necked RB flask equipped with a magnetic bar, a condenser and a nitrogen gas inlet, 2-bromo-6-methoxynaphthalene (7.32 g, 30 mmol), 4-methoxybenzene boronic acid (4.86 g, 32 mmol) and 1-propanol (50 mL) were mixed and stirred at room temperature for approx. 30 min. Palladium acetate (0.02 g, 0.09 mmol), triphenylphosphine (0.07 g, 0.27 mmol), Na2CO3 solution (2M, 18 mL, 36 mmol) and water (10 mL) were added and the mixture was refluxed for 1.5 h. When the mixture was still hot, 30 mL of water was added and the mixture was stirred and cooled to room temperature. The resultant crystals were filtered, washed with water and recrystallized from acetone to give the DMPN title compound as colorless flakes (6.86 g, 86%). mp 194–196° C. (DSC 196° C). 1H NMR (500 MHz, CDCl3) δ 3.88 (s, 3H), 3.95 (s, 3H), 7–8 (m, 10 H). IR (KBr) ν (cm−): 3058 (Ph-H, w), 1028 (OCH3, s). Anal. Calcd for C18H16O2: C, 81.79; H, 6.10. Found: C, 81.80; H, 6.25. GC-MS (m/z) 264 (M+).

Workup

  1. customIn an 100 mL three-necked RB flask equipped with a magnetic bar, a condenser and a nitrogen gas inlet
  2. temperaturethe mixture was refluxed for 1.5 h
  3. stirringthe mixture was stirred
  4. temperaturecooled to room temperature
  5. filtrationThe resultant crystals were filtered
  6. washwashed with water
  7. customrecrystallized from acetone

Sources & evidence

ORD record
ord-ccf7ed7aff114958b254416943f1d9f1
Source dataset
uspto-grants-2006_12
Patent number
US07148311B2

Reaction notes

Loading…