Acetyl chloride → Methyl 3-fluoro-4-nitrobenzoate

HRID 55378

Reaction equation

HRID 55378 reaction equation
[C:1](Cl)(=O)C.[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:9]([OH:11])=[O:10]>CO>[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:9]([O:11][CH3:1])=[O:10]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 592761Methyl 3-fluoro-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution prepared by the dropwise addition of 12 ml acetyl chloride to 150 ml methanol was added 7.0 grams 3-fluoro-4-nitrobenzoic acid and the resulting mixture was stirred at room temperature for 18 hours. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and 2% sodium carbonate solution. The organic layer was washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated in vacuo to give 6 grams of methyl 3-fluoro-4-nitrobenzoate as an orange oil which gradually hardened to a yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and 2% sodium carbonate solution
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-05ac5c8e382847e08303bf53883c12df
Source dataset
uspto-grants-1997_04
Patent number
US05624957

Linked notes

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