Reaktion #79591

ord-e87a45a954334f90abf8e26d8a47bc37

Reaktionsgleichung

O
water
O=C(O)c1cccc([N+](=O)[O-])c1Br
2-bromo-3-nitrobenzoic acid
CI
iodomethane
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
COC(=O)c1cccc([N+](=O)[O-])c1Br
methyl 2-bromo-3-nitrobenzoate
Ausbeute 96.0%

Edukte

O
water
O=C(O)c1cccc([N+](=O)[O-])c1Br
2-bromo-3-nitrobenzoic acid
CI
iodomethane
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe resultant precipitate was collected by filtration
  2. 2
    Sonstigedried in vacuo

Vorschrift

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 dimethylformamide was stirred at room temperature for 72 hours. The mixture was poured into 1.5 liters of water. 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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06713645B1uspto-grants-2004_03