Water → 4-Bromo-2-nitroanisole

HRID 1166236

Reaktionsgleichung

Reaktionsgleichung von HRID 1166236
[Br:1]Br.[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])([O-:5])=[O:4].O>C(O)(=O)C>[Br:1][C:10]1[CH:9]=[CH:8][C:7]([O:12][CH3:13])=[C:6]([N+:3]([O-:5])=[O:4])[CH:11]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 70482-NitroanisoleHCID 24408Bromine2×

Produkt 1

HCID 1185334-Bromo-2-nitroanisoleAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Bromine, Br2 (16 ml, 311 mmol) was added in small portions to a solution of 2-nitroanisole (17.1 ml, 140 mmol) in glacial acetic acid (80 ml). The reaction mixture was then heated at 60° C. for one hour. The reaction was poured into 400 ml water, and extracted with 600 ml diethyl ether/600 ml saturated NaHSO3 (aqueous). The organic layer was washed with NaHSO3 solution, then with water, dried over sodium sulfate, and concentrated under vacuum. The residue was recrystallized from diethyl ether to give 28.4 g (87%) of 4-bromo-2-nitroanisole. 1H NMR (300 MHz, CDCl3) δ7.970 (1H, d, J=2.5 Hz), 7.64 (1H, dd, J=8.9, 2.4 Hz), 7.00 (1H, d, J=8.9 Hz), 3.96 (3H, s).

Aufarbeitung

  1. extractionextracted with 600 ml diethyl ether/600 ml saturated NaHSO3 (aqueous)
  2. washThe organic layer was washed with NaHSO3 solution
  3. dry with materialwith water, dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-85b6ee239fb3408888e6833904d64cac
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613786B2

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