Dimethylformamide → 2-(2-Nitro-4-trifluoromethylphenoxy)-4-(1,1-dimethylpropyl)benzene

HRID 129876

Reaktionsgleichung

Reaktionsgleichung von HRID 129876
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9](O)=[CH:8][CH:7]=1)([CH3:5])[CH2:3][CH3:4].Br[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=1[N+:24]([O-:26])=[O:25].CN(C)C=[O:30]>>[N+:24]([C:15]1[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:14]=1[O:30][C:10]1[CH:11]=[C:6]([C:2]([CH3:5])([CH3:1])[CH2:3][CH3:4])[CH:7]=[CH:8][CH:9]=1)([O-:26])=[O:25]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 66434-tert-PentylphenolHCID 5207064-Bromo-3-nitrobenzotrifluoride

Produkt 1

HCID 539589052-(2-Nitro-4-trifluoromethylphenoxy)-4-(1,1-dimethylpropyl)benzene

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 4-(1,1-dimethylpropyl)phenol (821 mg, 0.005 mol), 4-bromo-3-nitrobenzotrifluoride (1.35g, 0.005 mol) potassium carbonate (1.38g, 0.010 mol) and cuprous oxide (143 mg, 0.001 mol) in dimethylformamide (25 ml) was stirred under argon at 150° C. for sixteen hours. The solvent was evaporated and the residue partitioned between ethyl acetate and water, the layers separated, dried over MgSO4 and evaporated. The crude product flash chromatographed (silica gel, ethyl acetate/hexane) to give the title compound as a yellow oil. 1H NMR (250 MHz, CDCl3) ∂8.20 (d, 1H), 7.70 (dd, 1H), 7.45 (m, 2H), 7.05 (m, 3H), 1.65 (q, 3H), 1.30 (s, 6H), 0.65 (t, 2H).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate and water
  3. customthe layers separated
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude product flash chromatographed (silica gel, ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-dd6cf062c803458ba3986245a309df08
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470882

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