Allyl bromide → 2-(Allyloxy)-4-methyl-1-nitrobenzene

HRID 1060230

Reaktionsgleichung

Reaktionsgleichung von HRID 1060230
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([O:8][CH2:14][CH:13]=[CH2:12])[CH:7]=1

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 127886-Nitro-m-cresol

Produkt 1

HCID 135756662-(Allyloxy)-4-methyl-1-nitrobenzeneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-methyl-2-nitrophenol (2.00 g, 13.1 mmol), allyl bromide (1.30 mL, 15.0 mmol), and cesium carbonate (5.5 g, 17 mmol) in DMF (100 mL) was stirred at ambient temperature. After 20 hrs the reaction was filtered, frit washed with methanol, and the filtrate evaporated in vacuo at 50° C. The residue was purified by flash column chromatography (4:1 then 2:1 hexane:ethyl acetate eluant) giving the title compound as a yellow oil (2.39 g, 95%) that crystallized after sitting 3 days at ambient temperature. 1H NMR (300 Mz, DCl3) δ 7.79 (d, 1H, J=8.2 Hz), 6.86 (s, 1H), 6.82 (m, 1H), 6.05 (ddt, 1H, J=17.3 Hz, 10.6 Hz, 5.0 Hz), 5.50 (ddd, 1H, J=17.3 Hz, 3.3 Hz, 1.7 Hz), 5.33 (ddd, 1H, J=10.6 Hz, 2.9 Hz, 1.5 Hz), 4.67 (dt, 2H, J=4,9 Hz, 1.6 Hz), 2.40 (s, 3H).

Aufarbeitung

  1. filtrationAfter 20 hrs the reaction was filtered
  2. washfrit washed with methanol
  3. customthe filtrate evaporated in vacuo at 50° C
  4. customThe residue was purified by flash column chromatography (4:1

Quellen und Nachweise

ORD-Eintrag
ord-e937650471254c9ca85f73f03af6a602
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521663B2

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