Methyl iodide → Methyl 4-fluoro-3-nitrobenzoate

HRID 1768555Notes

Reaction equation

HRID 1768555 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[F:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20]>CC(C)=O>[F:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([O:16][CH3:1])=[O:15])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (149 g, 1.08 mol) and iodomethane (252 mL, 4.05 mol) were added to a solution of 4-fluoro-3-nitrobenzoic acid (50 g, 0.27 mol) in dry acetone (700 mL) under argon. Overhead mechanical stirring was carried out for 16 hours. The reaction mixture was filtered, and acetone was removed under vacuum. The residue was partitioned between ethyl acetate and saturated potassium carbonate solution, the aqueous layer was washed with ethyl acetate, the combined organic layers were washed with saturated potassium carbonate solution, brine, dried over sodium sulfate, and concentrated to yield the title compound as a light yellow solid; m.p. 58.5°-59.50° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customacetone was removed under vacuum
  3. customThe residue was partitioned between ethyl acetate and saturated potassium carbonate solution
  4. washthe aqueous layer was washed with ethyl acetate
  5. washthe combined organic layers were washed with saturated potassium carbonate solution, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-765cca6980104dbc9995ce5884c11ecb
Source dataset
uspto-grants-1995_01
Patent number
US05378704

Reaction notes

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