Ethanol → Ethyl 2-fluoro-5-nitrobenzoate

HRID 1836815Notes

Reaction equation

HRID 1836815 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([O:6][CH2:19][CH3:20])=[O:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2809972-Fluoro-5-nitrobenzoic acid

Product 1

HCID 12793176Ethyl 2-fluoro-5-nitrobenzoateYield 84.3%

Conditions

Temperature
65 °C

Procedure

2-Fluoro-5-nitrobenzoic acid (1.85 g) was dissolved in ethanol (30 ml). Concentrated sulfuric acid (1.0 ml) was added to the solution, and the mixture was stirred at 65° C. overnight. The solvent was removed from the reaction solution by distillation under the reduced pressure, and the residue was adjusted to pH 7 by the addition of a saturated aqueous sodium hydrogencarbonate solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under the reduced pressure to give 1.79 g (84.3%) of ethyl 2-fluoro-5-nitrobenzoate.

Workup

  1. customThe solvent was removed from the reaction solution by distillation under the reduced pressure
  2. additionthe residue was adjusted to pH 7 by the addition of a saturated aqueous sodium hydrogencarbonate solution
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was then removed by distillation under the reduced pressure

Sources & evidence

ORD record
ord-a4b586770c654c04bb5e00dc709cd293
Source dataset
uspto-grants-2004_08
Patent number
US06777414B1

Reaction notes

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