Methanol → Methyl 2-fluoro-3-methylbenzoate

HRID 2369871Notes

Reaction equation

HRID 2369871 reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>>[F:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 27373792-Fluoro-3-methylbenzoic acid

Product 1

HCID 22049929Methyl 2-fluoro-3-methylbenzoateYield 83%

Procedure

To a stirred solution of 2-fluoro-3-methylbenzoic acid (4.0 g, 26.0 mmol) in anhydrous methanol (52 mL) at 0° C. was added thionyl chloride (2.8 mL, 39.0 mmol) dropwise and the reaction mixture was stirred overnight at reflux. The mixture was diluted with methanol and concentrated under reduced pressure to remove the excess thionyl chloride. The residue was then dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate, dried (Na2SO4), filtered, and concentrated under reduced pressure to give methyl 2-fluoro-3-methylbenzoate (3.6 g, 83%) as a clear oil that was used in the next step without further purification: 1H NMR (500 MHz, CDCl3) δ 7.75-7.72 (m, 1H), 7.38-7.35 (m, 1H), 7.26-7.06 (m, 1H), 3.91 (s, 3H), 2.31 (s, 3H).

Workup

  1. temperatureat reflux
  2. concentrationconcentrated under reduced pressure
  3. customto remove the excess thionyl chloride
  4. dissolutionThe residue was then dissolved in ethyl acetate
  5. washwashed with saturated aqueous sodium bicarbonate
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-739563413b144cde8ae422d4723a4821
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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