Methyl iodide → Methyl 2-fluoro-5-methylbenzoate

HRID 507151Notes

Reaction equation

HRID 507151 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].IC.[C:14](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2428292-Fluoro-5-methylbenzoic acid

Product 1

HCID 22645471Methyl 2-fluoro-5-methylbenzoateYield 82.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Heat a mixture of 2-fluoro-5-methyl-benzoic acid (1.0 g, 6.48 mmol), iodomethane (1.38 g, 9.73 mmol), and potassium carbonate (2.68 g, 19.44 mmol) in acetone (20 mL) at reflux overnight. Cool the reaction and filter through Celite®. Concentrate the filtrate under reduced pressure to provide the title compound as a colorless gum (0.895 g, 82%). 1H NMR (CDCl3, 300 MHz) δ 2.32 (s, 3H), 3.89 (s, 3H), 6.95-7.10 (m, 1H), 7.20-7.30 (m 1H), 7.75-7.80 (m, 1H); TLC Rf=0.45 (2:1 Hexanes/Ethyl Acetate).

Workup

  1. temperatureHeat
  2. temperatureat reflux overnight
  3. temperatureCool
  4. customthe reaction
  5. filtrationfilter through Celite®
  6. concentrationConcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-b68cc76b145049f69905750ea26400a1
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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