Ethanol → Ethyl 2-fluoro-5-nitrobenzoate

HRID 1925935Notes

Reaction equation

HRID 1925935 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].[CH2:18](O)[CH3:19]>>[F:5][C:6]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:7]=1[C:8]([O:10][CH2:18][CH3:19])=[O:9]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 2809972-Fluoro-5-nitrobenzoic acid

Product 1

HCID 12793176Ethyl 2-fluoro-5-nitrobenzoate

Conditions

Temperature
80 °C

Procedure

Under ice-cooling, thionyl chloride (8.02 mL) was added dropwise to ethanol (200 mL), and 2-fluoro-5-nitrobenzoic acid (13.81 g) was added. This mixture was stirred at 80° C. for 4 hrs. and concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (15.77 g) as a pale-yellow oil.

Workup

  1. temperatureUnder ice-cooling
  2. additionwas added
  3. concentrationand concentrated under reduced pressure
  4. additionA saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b21913ec3aa142d2bff986649b8cd43f
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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