Methanol → Methyl 2-chloro-3-nitrobenzoate

HRID 2168519Notes

Reaction equation

HRID 2168519 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].S(Cl)(Cl)=O.[CH3:18]O>>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 6931527HCID 6931527, compound

Product 1

HCID 10751184Methyl 2-chloro-3-nitrobenzoateYield 98%

Procedure

To a stirred solution of 2-chloro-3-nitrobenzoate (1.0 g, 5.0 mmol) in anhydrous methanol (10 mL) at 0° C. was added thionyl chloride (0.5 mL, 7.4 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 and then re-dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate, re-extracted with ethyl acetate, dried (Na2SO4), filtered, and concentrated under reduced pressure to give methyl 2-chloro-3-nitrobenzoate (1.1 g, 98%) as a white foam that was used in the next step without further purification: 1H NMR (300 MHz, DMSO-d6) δ 8.21 (d, J=1.5 Hz, 1H), 8.07 (dd, J=7.8, 1.5 Hz, 1H), 7.73 (t, J=8.1 Hz, 1H), 3.91 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-205c73223e594b00a87c0a385ec27723
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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