Cesium carbonate → 4'-Fluoro-4-methylbiphenyl-3-amine

HRID 1963986

Reaktionsgleichung

Reaktionsgleichung von HRID 1963986
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)O1.Br[C:18]1[CH:19]=[CH:20][C:21]([CH3:25])=[C:22]([CH:24]=1)[NH2:23].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:18]2[CH:19]=[CH:20][C:21]([CH3:25])=[C:22]([NH2:23])[CH:24]=2)=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27348055-Bromo-o-toluidineHCID 27605932-(4-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 463144304'-Fluoro-4-methylbiphenyl-3-amineAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

5.0 g (22.5 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-fluorobenzene, 1.87 mL (15 mmol) of 5-bromo-2-methylaniline, 1.73 g (1.5 mmol) of tetrakis(triphenyl phosphine)palladium (0), and 7.33 g (15 mmol) of cesium carbonate were heated under reflux for 8 hours in 150 mL of THF. After completion of the reaction, THF was distilled off under reduced pressure, and ethyl acetate was added to separate the solid by filtration. The organic layer was then washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled off under reduced pressure. The resulting crude product was separated and purified using silica gel column chromatography, thereby giving 4′-fluoro-4-methylbiphenyl-3-amine (yield: 43%).

Aufarbeitung

  1. distillationwas distilled off under reduced pressure, and ethyl acetate
  2. additionwas added
  3. customto separate the solid
  4. filtrationby filtration
  5. washThe organic layer was then washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThereafter, the solvent was distilled off under reduced pressure
  8. customThe resulting crude product was separated
  9. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-06a31f7821b24146988f04d108ea49f6
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415479B2

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