Sodium Carbonate → 6-(4-Methoxyphenyl)naphthalene-2-carboxylic acid

HRID 858333Notes

Reaction equation

HRID 858333 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=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>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]3)=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 201262(4-Methoxyphenyl)boronic acidHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 150998986-(4-Methoxyphenyl)naphthalene-2-carboxylic acidYield 81%

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, 6-bromo-2-naphthoic acid (2.62 g, 96%, 10 mmol), 4-methoxy-benzeneboronic acid (1.52 g, 10 mmol) and 1-propanol (20 mL) were mixed and stirred at room temperature for about 30 min. Palladium acetate (0.007 g, 0.003 equiv., 0.03 mmol), triphenylphosphine (0.024 g, 0.009 equiv., 0.9 mmol), Na2CO3 solution (2 M, 8 mL, 1.20 equiv., 12 mmol) and water (4 mL) were added and the mixture was refluxed for 2 h. When the mixture was still hot, 20 mL of water was added and the mixture was stirred and cooled to room temperature. The resultant crystals were filtered, washed with water and refluxed with 50 mL of acetic acid for 3–4 h. A white solid was obtained (2.55 g) and recrystallization from acetone gave the title compound as white crystals (2.24 g, 81%): mp 267–269° C.

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 2 h
  3. stirringthe mixture was stirred
  4. temperaturecooled to room temperature
  5. filtrationThe resultant crystals were filtered
  6. washwashed with water
  7. temperaturerefluxed with 50 mL of acetic acid for 3–4 h
  8. customA white solid was obtained
  9. custom(2.55 g) and recrystallization from acetone

Sources & evidence

ORD record
ord-9826da25b5fa4b07940a75b90b548d8e
Source dataset
uspto-grants-2006_12
Patent number
US07148311B2

Reaction notes

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