Sodium Carbonate → HCID 23594024, compound

HRID 1612049Notes

Reaction equation

HRID 1612049 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1Cl.[CH3:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[C:5]1[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:14]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10751184Methyl 2-chloro-3-nitrobenzoateHCID 15852636HCID 15852636, compound

Product 1

HCID 23594024HCID 23594024, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-3-nitrobenzoic acid methyl ester, (2.16 g, 10.0 mM), 1-methoxynaphthalene-2-boronic acid, (2.22 g, 11.0 mM), tetrakis(triphenylphosphine) palladium(0)(0.584 g, 0.5 mM), and 2M aqueous sodium carbonate solution (10.5 mL, 21.0 mM) in THF (50 mL) was stirred at reflux for 31 h in the absence of light. The mixture was cooled to room temperature, the THF removed in vacuo, and the resulting aqueous residue dissolved in ethyl acetate and brine. The solvent layers were separated, the aqueous layer extracted with ethyl acetate (4×25 mL), the combined ethyl acetate extracts washed successively with H2O, 1N HCl, saturated aqueous NaHCO3 solution, and saturated brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resultant oil was purified by column chromatography on silica gel (elution with 1:1 chloroform/toluene) to afford 2.54 g (75%) of the title compound 2-(1-methoxynaphthalen-2-yl)-3-nitrobenzoic acid, methyl ester as a yellow solid (MP 139–141° C., MW 337.34).

Workup

  1. temperatureat reflux for 31 h in the absence of light
  2. customthe THF removed in vacuo
  3. dissolutionthe resulting aqueous residue dissolved in ethyl acetate
  4. customThe solvent layers were separated
  5. extractionthe aqueous layer extracted with ethyl acetate (4×25 mL)
  6. washthe combined ethyl acetate extracts washed successively with H2O, 1N HCl, saturated aqueous NaHCO3 solution, and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resultant oil was purified by column chromatography on silica gel (elution with 1:1 chloroform/toluene)

Sources & evidence

ORD record
ord-6b36cf20d527440cbd9fc501488ead63
Source dataset
uspto-grants-2006_01
Patent number
US06992100B2

Reaction notes

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