Allyl bromide → 2-(Allyloxy)-5-chloro-4-nitroaniline

HRID 1373748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1373748
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[CH2:13](Br)[CH:14]=[CH2:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:15]([O:12][C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[C:6]([Cl:8])=[CH:7][C:2]=1[NH2:1])[CH:14]=[CH2:13]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 38948482-Amino-4-chloro-5-nitrophenol

Produkt 1

HCID 210753742-(Allyloxy)-5-chloro-4-nitroanilineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 2-amino-4-chloro-5-nitrophenol (10 g, 0.053 mol) and allyl bromide (5.05 mL, 0.058 mol) in DMF (100 mL) was added K2CO3. The reaction mixture was stirred at room temperature for 3 hours, and then the inorganic salts were filtered off. The filtrate was concentrated, and the residue was dissolved in ethyl acetate and washed with aqueous NH4Cl. The organic layer was dried over MgSO4 and concentrated to provide the desired product (10.9 g, 90%) as yellow solid. MS (DCI/NH3) m/z 246.04 (M+NH4)+; 1H NMR (500 MHz, DMSO-D6) δ ppm 4.68 (d, J=4.99 Hz, 2 H) 5.29 (dd, J=10.60, 1.56 Hz, 1 H) 5.48 (dd, J=17.47, 1.56 Hz, 1 H) 6.05 (m, 1 H) 6.48 (s, 2 H) 6.76 (s, 1 H) 7.59 (s, 1 H).

Aufarbeitung

  1. filtrationthe inorganic salts were filtered off
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with aqueous NH4Cl
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-51fc89982ebc4072a37de9ff7be24c7f
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07163939B2

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