Methanol → Methyl 2-fluoro-4-methoxy-5-nitrobenzoate

HRID 488498Notes

Reaction equation

HRID 488498 reaction equation
[Na].[CH3:2][O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[F:14].[CH3:16][OH:17]>>[CH3:2][O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:17][CH3:16])=[CH:7][C:6]=1[F:14]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 5360545SodiumHCID 11217860Methyl 2-Fluoro-5-nitrobenzoate

Product 1

HCID 23404649Methyl 2-fluoro-4-methoxy-5-nitrobenzoateYield 17%

Conditions

Temperature
0 °C

Procedure

A mixture of sodium metal (1.27 g, 0.055 mol) and MeOH (250 mL) was stirred at 0° C. for 10 minutes. This solution was added to a solution of 2-fluoro-5-nitrobenzoic acid methyl ester (10.0 g, 0.046 mol) in MeOH (250 mL), and the mixture was stirred for 20 minutes at 0° C. to 5° C. The reaction mixture was then allowed to warm to room temperature and stir for 2 hours. The mixture was then filtered to give an off-white precipitate. Recrystallization with CHCl3 (70 ml) yielded an off-white crystalline solid, 1.825 g (0.008 mol, 17%) of the title compound.

Workup

  1. stirringthe mixture was stirred for 20 minutes at 0° C. to 5° C
  2. temperatureto warm to room temperature
  3. stirringstir for 2 hours
  4. filtrationThe mixture was then filtered
  5. customto give an off-white precipitate
  6. customRecrystallization with CHCl3 (70 ml)

Sources & evidence

ORD record
ord-5ff46d7eb75f4c939145779bbbe6d847
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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