Sodium Carbonate → HCID 23220910, compound

HRID 858332Notes

Reaction equation

HRID 858332 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]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)([OH:16])=[O:15].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>[C:14]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=3)[CH:3]=2)=[CH:19][CH:18]=1)([OH:16])=[O:15]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 787862-Bromo-6-methoxynaphthaleneHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 23220910HCID 23220910, compound

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 (4.74 g, 20 mmol), 4-carboxybenzene boronic acid (3.50 g, 20 mmol) and 1-propanol (40 mL) were mixed and stirred at room temperature for approximately 30 min. Palladium acetate (0.014 g, 0.003 equiv., 0.06 mmol), triphenylphosphine (0.047 g, 0.009 equiv., 0.18 mmol), Na2CO3 solution (2M, 12 mL, 1.20 equiv., 24 mmol) and water (8 mL) were added and the mixture was refluxed for 1.5 h. When the mixture was still hot, 25 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 (5.08 g) and recrystallization from acetone showed the title compound as white crystals (4.63 g, 83%). mp 288–289° C. 1H NMR (500 MHz, DMSO) δ 3.90 (s, 3H), 7.2–8.3 (m, 10H), 12.99 (s, 1H). IR (KBr) ν (cm−1): 2500–3000 (COO—H, very broad, m), 1030 (OCH3, s), 1678 (C═O, s). Anal. Calcd for C18H14O3: C, 77.68; H, 5.07. Found: C, 77.56; H, 5.08.

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. temperaturerefluxed with 50 mL of acetic acid for 3–4 h
  8. customA white solid was obtained
  9. custom(5.08 g) and recrystallization from acetone

Sources & evidence

ORD record
ord-088f35115aa04f36b21c3ba9ea9fdd54
Source dataset
uspto-grants-2006_12
Patent number
US07148311B2

Reaction notes

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