Sodium Carbonate → HCID 19876535, compound

HRID 2250545Notes

Reaction equation

HRID 2250545 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.[C:15]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([OH:17])=[O:16].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:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:21]3[CH:22]=[CH:23][C:18]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=3)[CH:3]=2)[CH:8]=1)([OH:14])=[O:13]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 3121834-Carboxyphenylboronic AcidHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 19876535HCID 19876535, 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, 6-bromo-2-naphthoic acid (2.51 g, 10 mmol), 4-carboxybenzene boronic acid (1.66 g, 10 mmol) and 20 mL of 1-propanol 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 1.5 h. When the mixture was still hot, 20 mL of water was added and the mixture was stirred and cooled to room temperature. The solid was separated by filtration and refluxed with 2 mL of 1 M HCl and 25 mL of acetic acid. A white solid was obtained after filtration. No melting point was detected up to 350° C. 1H NMR (500 MHz, DMSO) δ 7.9-8.7 (m, 10H), 13.1 (s, 2H). IR (KBr) ν (cm−1): Anal. Calcd for C18H12O4: C, 73.97; H, 4.14. Found: C, 73.59; H, 4.05.

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. customThe solid was separated by filtration
  6. temperaturerefluxed with 2 mL of 1 M HCl and 25 mL of acetic acid
  7. customA white solid was obtained
  8. filtrationafter filtration
  9. customwas detected up to 350° C

Sources & evidence

ORD record
ord-98e530d1cad4457e8eb3be89f71ed1a3
Source dataset
uspto-grants-2008_01
Patent number
US07317066B2

Reaction notes

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