Methanol → Methyl 2-fluoro-3-methylbenzoate

HRID 2168492Notes

Reaction equation

HRID 2168492 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-0c5bef2b212e4f69af770f405f8db939
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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