3-Hydroxybenzaldehyde → 3-(2,2,2-Trifluoroethoxy)benzaldehyde

HRID 594277

Reaktionsgleichung

Reaktionsgleichung von HRID 594277
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].FC(F)(F)S(O[CH2:16][C:17]([F:20])([F:19])[F:18])(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C.CCOC(C)=O>[F:18][C:17]([F:20])([F:19])[CH2:16][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Komponenten

7

Edukt 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Produkt 1

HCID 47709473-(2,2,2-Trifluoroethoxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of commercially available 3-hydroxybenzaldehyde (2.000 g; 16.40 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (4.561 g; 19.70 mmol), and Cs2CO3 (8.004 g; 24.60 mmol) in anh. DMF (30 ml) was stirred at rt, under nitrogen, for 1 h. Water and AcOEt were added and the organic layer was washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 3-(2,2,2-trifluoroethoxy)benzaldehyde as a colorless oil. LC-MS (conditions A): tR=0.75 min.; no ionisation.

Aufarbeitung

  1. washthe organic layer was washed with water
  2. dry with materialdried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e3345cc72e124942a2d716b44c65b085
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242970B2

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