Water → Methyl 2-bromo-3-nitrobenzoate

HRID 51347

Reaktionsgleichung

Reaktionsgleichung von HRID 51347
[Br:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].IC.[C:16](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 684522-Bromo-3-nitrobenzoic acid

Produkt 1

HCID 79263Methyl 2-bromo-3-nitrobenzoateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-bromo-3-nitrobenzoic acid (28.4 g, 115.0 mM), iodomethane (18.0 g, 127 mM), and potassium carbonate (19.0 g, 137.4 mM) in 100 mL DMF was stirred at room temperature for 72 hours. The mixture was poured into 1.5 liters of H2O. The resultant precipitate was collected by filtration and dried in vacuo to afford 28.79 g (96%) of methyl 2-bromo-3-nitrobenzoate as a white solid. 1H NMR (DMSO-d6) δ8.3 (dd, 1H, J=1 and 8 Hz), 7.9 (dd, 1H, J=1 and 8 Hz), 7.7 (t, 1H, J=8 Hz), and 3.9 (s, 3H). IR (KBr, cm−1) 2950, 1738, 1541, 1435, 1364, 1298, and 1142. MS (FD) m/e 259, 261.

Aufarbeitung

  1. filtrationThe resultant precipitate was collected by filtration
  2. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ba87d28dc6b640a79666c93c428bec57
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713645B1

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