Sodium Carbonate → 7-(4-Acetylphenyl)-3-hydroxynaphthalene-2-carboxylic Acid

HRID 1361008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361008
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([OH:15])[C:8]([C:12]([OH:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[C:16]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)(=[O:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:16]([C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([OH:15])[C:8]([C:12]([OH:14])=[O:13])=[CH:9]3)=[CH:4][CH:3]=2)=[CH:21][CH:20]=1)(=[O:18])[CH3:17]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 745032-Naphthalenecarboxylic acid, 7-bromo-3-hydroxy-HCID 37021224-Acetylphenylboronic acid

Produkt 1

HCID 574570427-(4-Acetylphenyl)-3-hydroxynaphthalene-2-carboxylic AcidAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

To 7-bromo-3-hydroxynaphthalene-2-carboxylic acid (100 mg, 0.37 mmol) (example 340) was added a solution of 4-acetylphenylboronic acid (92 mg, 0.56 mmol) in acetone (2.2 mL) followed by a solution of sodium carbonate (198 mg, 1.87 mmol) in water (3.3 mL). A suspension of palladium(II) acetate (4 mg, 0.02 mmol) in acetone (0.5 mL) was filtered and added to the above solution. The mixture was purged with N2 and stirred vigorously for 24 hours at room temperature. The reaction mixture was poured into 1 N hydrochloric acid (aq.) (60 mL) and the precipitate was filtered off and rinsed with water (3×40 mL). The crude product was dissolved in acetone (25 mL) and dried with magnesium sulfate (1 h). Filtration followed by concentration furnished the title compound as a solid (92 mg). 1H-NMR (DMSO-d6): δ 12.60 (1H, bs), 8.64 (1H, s), 8.42 (1H, s), 8.08 (2H, d), 7.97 (2H, d), 7.92 (2H, m), 7.33 (1H, s), 2.63 (3H, s); HPLC-MS (Method (A): m/z: 307 (M+1); Rt=3.84 min.

Aufarbeitung

  1. filtrationwas filtered
  2. additionadded to the above solution
  3. customThe mixture was purged with N2
  4. additionThe reaction mixture was poured into 1 N hydrochloric acid (aq.) (60 mL)
  5. filtrationthe precipitate was filtered off
  6. washrinsed with water (3×40 mL)
  7. dissolutionThe crude product was dissolved in acetone (25 mL)
  8. dry with materialdried with magnesium sulfate (1 h)
  9. filtrationFiltration
  10. concentrationfollowed by concentration

Quellen und Nachweise

ORD-Eintrag
ord-cb16a0ff8bd14ee693e79a2700529384
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879893B2

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