Methanol → Methyl 2-fluoro-4-methoxybenzoate

HRID 1802411Notes

Reaction equation

HRID 1802411 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:17]O>>[CH3:17][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:2]=1[F:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27745422-Fluoro-4-methoxybenzoic acid

Product 1

HCID 21255685Methyl 2-fluoro-4-methoxybenzoateYield 92%

Procedure

To a solution of 5.0 g (29.4 mmol) of 2-fluoro-4-methoxybenzoic acid in methanol (50 mL) at room temperature are added 2.13 mL (29.4 mmol) of thionyl chloride. The reaction is stirred at room temperature for 16 h and the solvent is removed under reduced pressure. The residue is dissolved in DCM and washed with brine. The organic layer is dried (MgSO4), filtered and the filtrate is concentrated under reduced pressure to give 5.04 g (27.1 mmol) of 2-fluoro-4-methoxybenzoic acid methyl ester. Yield: 92%, ES-MS: m/z 185 [M+H].

Workup

  1. customthe solvent is removed under reduced pressure
  2. dissolutionThe residue is dissolved in DCM
  3. washwashed with brine
  4. dry with materialThe organic layer is dried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-56ce745bdaee476c8ce8c4ac80d883bf
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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