Water → [3-(2-Chloro-4-trifluoromethylphenoxymethyl)oxetan-3-yl]-methanol

HRID 535265

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:14][C:15]1([CH2:19][OH:20])[CH2:18][O:17][CH2:16]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:5]=[CH:6][C:7]=1[O:8][CH2:14][C:15]1([CH2:19][OH:20])[CH2:18][O:17][CH2:16]1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

600 mg of 3-chloro-4-hydroxybenzotrifluoride and 829 mg of 3-bromomethyl-3-oxetanemethanol were dissolved in 20 ml of acetonitrile, and 1.49 g of cesium carbonate were added. The reaction mixture was heated to 110° C. and stirred at this temperature for three hours. 50 ml of water and 50 ml of ethyl acetate were added to the cooled reaction mixture. The organic phase was removed, dried over MgSO4 and then concentrated under reduced pressure. The residue was purified on silica gel with the n-heptane/ethyl acetate solvent mixture as a linear gradient of 100% n-heptane=>100% ethyl acetate. This gave 990 mg of [3-(2-chloro-4-trifluoromethylphenoxymethyl)oxetan-3-yl]methanol.

Aufarbeitung

customThe organic phase was removed
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified on silica gel with the n-heptane/ethyl acetate solvent mixture as a linear gradient of 100% n-heptane=>100% ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-ee84e78adf8f46ed9d0860a704466fc9
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08859494B2

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