2-Hydroxy-5-(trifluoromethoxy)benzaldehyde → 2-(1-Phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)benzaldehyde

HRID 323755

Reaktionsgleichung

Reaktionsgleichung von HRID 323755
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[CH:4]=[O:5].I[C:16]1([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:17]1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(=O)([O-])[O-].[Ag+2]>[C:20]1([S:19][C:16]2([O:1][C:2]3[CH:9]=[CH:8][C:7]([O:10][C:11]([F:12])([F:13])[F:14])=[CH:6][C:3]=3[CH:4]=[O:5])[CH2:18][CH2:17]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 2

HCID 12680582-Hydroxy-5-(trifluoromethoxy)benzaldehydeHCID 11000298(1-Iodocyclopropyl)(phenyl)sulfane

Produkt 1

HCID 215840782-(1-Phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)benzaldehydeAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Silver carbonate (1.2 g, 4.34 mmol) was added to a solution of 2-hydroxy-5-(trifluoromethoxy)benzaldehyde (0.5 g, 2.43 mmol) and (1-iodocycloprop-1-yl)phenylsulfide (Cohen T. and Matz J. R., J. Am. Chem. Soc. 1980, 102, 6902) (1.2 g, 4.34 mmol) in toluene (30 mL) and the mixture was stirred at 40° C. overnight. The mixture was cooled, diluted with ethyl acetate and filtered, washing well with ethyl acetate. The mixture was washed with aqueous sodium hydroxide, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/Et2O (95:5), to give the title compound as a yellow oil (191 mg, 27%). 1H NMR (360 MHz, CDCl3) δ1.51-1.56 (2H, m), 1.44-1.48 (2H, m), 7.25-7.35 (7H, m), 7.69 (1H, d, J 2.0 Hz), and 10.26 (1H, s).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washwashing well with ethyl acetate
  4. washThe mixture was washed with aqueous sodium hydroxide
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with hexane/Et2O (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-a8adc5e8d0934517b8299d7ddcc3da30
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06214846B1

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