Water → Methyl 2-fluoro-3-nitrobenzoate

HRID 1046794Notes

Reaction equation

HRID 1046794 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-a99b2deb5af346a18cf44f1f7fa89f11
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

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