Hydrochloric Acid → Methyl 3-fluoro-4-nitrobenzoate

HRID 1452949Notes

Reaction equation

HRID 1452949 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[CH3:14]O.Cl>CCOCC>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH3:14])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 592761Methyl 3-fluoro-4-nitrobenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-fluoro-4-nitrobenzoic acid (5.00 g, 27.0 mmol), Methanol (40 mL), and 2 N HCl in Et2O was heated at reflux for 16 hr. Volatile material was removed under vacuum. The residue was diluted with AcOEt (150 mL), washed successively with saturated NaHCO3 solution and brine, and dried over anhydrous MgSO4. Evaporation of solvent under vacuum gave the title compound (5.18 g, 96% yield) as a pale yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hr
  3. customVolatile material was removed under vacuum
  4. additionThe residue was diluted with AcOEt (150 mL)
  5. washwashed successively with saturated NaHCO3 solution and brine
  6. dry with materialdried over anhydrous MgSO4
  7. customEvaporation of solvent under vacuum

Sources & evidence

ORD record
ord-af3d681c3f1445cc94bfdbf03598e815
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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