Methanol → Methyl 2,5-difluorobenzoate
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:2]=1[F:1]Participants
4
Conditions
- Temperature
- 60 °C
Procedure
To a stirred solution of 2,5-difluorobenzoic acid (20 g, 126 mmol) in MeOH (250 mL) is added thionyl chloride (22.5 g, 190 mmol) dropwise at ice-cold conditions. After complete addition the reaction mixture is heated at 60° C. for 3 h. The reaction mixture is concentrated and the residue neutralized with aqueous Na2CO3 solution. It is extracted with CH2Cl2 (3×100 mL), dried over anhydrous MgSO4 and concentrated under reduced pressure to afford the desired 2,5-difluorobenzoic acid methyl ester as a thick liquid (22 g).
Workup
- additionAfter complete addition the reaction mixture
- concentrationThe reaction mixture is concentrated
- extractionIt is extracted with CH2Cl2 (3×100 mL)
- dry with materialdried over anhydrous MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-47eb7b5be8ec489ab2048afed9441841
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362249B2
Reaction notes
Loading…