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

HRID 580841

Reaktionsgleichung

[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

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) δ 1.51-1.56 (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

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

Quellen und Nachweise

ORD-Eintrag: ord-89ab6082b0be4ac28048b897d1425c2e
Quelldatensatz: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05919781

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