Water → Methyl 2-fluoro-3-nitrobenzoate

HRID 2061123Notes

Reaction equation

HRID 2061123 reaction equation
[F-:1].[Cs+].[CH3:3][O:4][C:5](=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1Cl.O>CS(C)=O>[CH3:3][O:4][C:5](=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[F:1]

Participants

5

Reactant 3

HCID 962WaterHCID 25953Cesium fluorideHCID 10751184Methyl 2-chloro-3-nitrobenzoate

Product 1

HCID 13470961Methyl 2-fluoro-3-nitrobenzoateYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

Cesium fluoride (11.2 g) was added to a solution of 2-chloro-3-nitrobenzoic acid methyl ester (10.6 g, 49.0 mmol) in DMSO (49 mL), and the mixture was stirred at 140° C. for 40 minutes. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic extract was washed in series with water and saturated saline, and dried over magnesium sulfate. The title compound (9.23 g, 95%) was then obtained by vacuum concentration as a pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed in series with water and saturated saline
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-3b844ab4c39d4a7c98fb481a2754b5cd
Source dataset
uspto-grants-2012_10
Patent number
US08278465B2

Reaction notes

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