Toluene → (2-(2,2,2-Trifluoroethoxy)-phenyl)-aniline

HRID 2101204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2101204
[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1Br.C1(C)C=CC=CC=1.[NH2:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 226154791-Bromo-2-(2,2,2-trifluoroethoxy)benzene

Produkt 1

HCID 20080993(2-(2,2,2-Trifluoroethoxy)-phenyl)-aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 1.0 g (3.93 mmol) of 2-trifluoroethoxyphenyl bromide (Example 3, Step A) in 39 Ml of toluene was added 0.136 g (0.118 mmol) of tetrakis(triphenylphosphine)palladium(0), 0.56 g (4.31 mol) of 3-aminophenylboronic acid, 47 Ml (94.1 mmol) of a 2M solution of sodium carbonate and 8 Ml of ethanol and the reaction mixture was heated at 90° C. for 22 hr. The reaction mixture was cooled to RT, and partitioned between water and EtOAc. The aqueous fraction was extracted with EtOAc and the combined organic fractions were washed with water and brine and dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, 4:1 hexanes:EtOAc) to give the title compound. Mass Spectrum (ESI) m/e M+1 268.1.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to RT
  2. custompartitioned between water and EtOAc
  3. extractionThe aqueous fraction was extracted with EtOAc
  4. washthe combined organic fractions were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by chromatography (silica, 4:1 hexanes:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-955512a14f464e1ca11e5d1709d404f8
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572822B2

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