2-Bromopropane → Isopropyl 4-isopropoxy-3-(trifluoromethyl)benzoate

HRID 515700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515700
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[C:15](=O)([O-])[O-].[Cs+].[Cs+].Br[CH:22]([CH3:24])[CH3:23].[CH3:25][C:26](N(C)C)=O>>[CH:22]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH:26]([CH3:25])[CH3:15])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14])([CH3:24])[CH3:23]

Komponenten

5

Edukt 4

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 27751124-Hydroxy-3-(trifluoromethyl)benzoic acid

Produkt 1

HCID 59201795Isopropyl 4-isopropoxy-3-(trifluoromethyl)benzoate

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 4-hydroxy-3-(trifluoromethyl)benzoic acid (14.55 mmol) and cesium carbonate (43.7 mmol) in DMA (60 mL) was added 2-bromopropane (36.4 mmol). The reaction was stirred at 80° C. for 16 h. The mixture was filtered through celite and concentrated under vacuum. The residue was dissolved in EtOAc and washed with water, then brine, then dried over MgSO4, and filtered. The solvent was removed under vacuum to give the title compound as a light yellow oil (13.1 mmol). 1H NMR (400 MHz, CDCl3) δ ppm 1.36 (d, J=6.32 Hz, 6H), 1.39 (d, J=6.06 Hz, 6H), 4.72 (septet, J=6.06 Hz, 1H), 5.24 (septet, J=6.25 Hz, 1H), 7.00 (d, J=8.84 Hz, 1H), 7.26 (s, OH), 8.15 (dd, J=8.72, 2.15 Hz, 1H), 8.23 (d, J=2.15 Hz, 1H).

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialbrine, then dried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9981af631bc54817bb8e387e9116ac2e
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108969B2

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