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

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.

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

ORD record

ord-5b58462419e64a5ebd6404242c4536e7

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07317066B2