Potassium Phosphate, Tribasic → Perfluorophenyl 5-(2-methoxy-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate

HRID 1473297

Reaktionsgleichung

Reaktionsgleichung von HRID 1473297
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([O:15][C:16]1[C:21]([F:22])=[C:20]([F:23])[C:19]([F:24])=[C:18]([F:25])[C:17]=1[F:26])(=[O:14])=[O:13])=[CH:7]2.[CH3:27][O:28][C:29]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][C:30]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>>[CH3:27][O:28][C:29]1[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=[CH:31][C:30]=1[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([O:15][C:16]1[C:21]([F:22])=[C:20]([F:23])[C:19]([F:24])=[C:18]([F:25])[C:17]=1[F:26])(=[O:13])=[O:14])=[CH:7]2

Komponenten

4

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 24901776(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acidHCID 86687354Perfluorophenyl 5-bromonaphthalene-2-sulfonate

Produkt 1

HCID 86687355Perfluorophenyl 5-(2-methoxy-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonateAusbeute 65,9 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A vial was charged with perfluorophenyl 5-bromonaphthalene-2-sulfonate (285.84 mg, 0.631 mmol), (2-methoxy-4-(trifluoromethyl)phenyl)boronic acid (277 mg, 1.261 mmol), potassium phosphate (402 mg, 1.892 mmol), and Pd(AmPhos)2Cl2 (22.33 mg, 0.032 mmol). The vial was flushed with Ar (g), then dioxane (1577 μl) and water (526 μl) was added. The vial was sealed and heated in a microwave for 20 min at 90° C. The mixture was diluted with water and extracted with EtOAc (three times). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The product was purified by chromatography on silica gel (0 to 20% EtOAc/Heptane) to give perfluorophenyl 5-(2-methoxy-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate (228.1 mg, 0.416 mmol) as a white foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=8.62 (d, J=1.9 Hz, 1H), 8.07 (d, J=8.2 Hz, 1H), 7.85 (dd, J=2.0, 9.0 Hz, 1H), 7.79-7.71 (m, 2H), 7.64 (dd, J=1.3, 7.1 Hz, 1H), 7.47-7.38 (m, 2H), 7.29 (s, 1H), 3.77 (s, 3H).

Aufarbeitung

  1. customThe vial was flushed with Ar (g)
  2. additiondioxane (1577 μl) and water (526 μl) was added
  3. customThe vial was sealed
  4. additionThe mixture was diluted with water
  5. extractionextracted with EtOAc (three times)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by chromatography on silica gel (0 to 20% EtOAc/Heptane)

Quellen und Nachweise

ORD-Eintrag
ord-5d338ddd298b4d9c93fecbeb3809b906
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012443B2

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