Water → alpha-(4-Fluorophenyl)-4-(trifluoromethyl)benzenemethanol

HRID 561418

Reaktionsgleichung

Reaktionsgleichung von HRID 561418
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.C([Li])CCC.[F:14][C:15]([F:25])([F:24])[C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][CH:17]=1.O>O1CCCC1.CCCCCC.ClCCl>[F:8][C:5]1[CH:6]=[CH:7][C:2]([CH:22]([C:19]2[CH:18]=[CH:17][C:16]([C:15]([F:14])([F:24])[F:25])=[CH:21][CH:20]=2)[OH:23])=[CH:3][CH:4]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 99931-Bromo-4-fluorobenzeneHCID 679964-(Trifluoromethyl)benzaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 579773alpha-(4-Fluorophenyl)-4-(trifluoromethyl)benzenemethanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

1.00 g (5.71 mmol) of 4-bromofluorobenzene were dissolved in 10 ml of tetrahydrofuran at −78° C. Addition of 2.2 ml (6.86 mmol) of a 1.6N solution of n-butyllithium in hexane was followed by stirring for 15 min, and then 1.26 g (6.86 mmol) of trifluoro-p-tolualdehyde dissolved in 10 ml of tetrahydrofuran were added dropwise. The mixture was stirred at −78° C. for 1 h and then at RT for 1 h. The reaction solution was mixed with water and dichloromethane, and the phases were separated. The aqueous phase was extracted with dichloromethane, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered, and the solvents were removed in vacuo. The crude product was purified by preparative HPLC (mobile phase: acetonitrile-water gradient). 1.02 g (66% of theory) of the title compound were obtained.

Aufarbeitung

  1. additionwere added dropwise
  2. stirringThe mixture was stirred at −78° C. for 1 h
  3. waitat RT for 1 h
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. washthe combined organic phases were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvents were removed in vacuo
  10. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile-water gradient)

Quellen und Nachweise

ORD-Eintrag
ord-747f0697c3b5470eb5ef7c40241ce08a
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

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