Cesium fluoride → Methyl 2-fluoro-3-nitrobenzoate

HRID 1053611Notes

Reaction equation

HRID 1053611 reaction equation
[F-:1].[Cs+].Cl[C:4]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]>CN(C)C=O>[F:1][C:4]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

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

Product 1

HCID 13470961Methyl 2-fluoro-3-nitrobenzoateYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Cesium fluoride (499.02 g, 3.19 mol) was added into a flask equipped with a stirrer under a nitrogen gas stream, and was agitated for one hour at 110° C. Methyl 2-chloro-3-nitrobenzoate (229.00 g, 1.06 mol) and N,N-dimethylformamide (2000 ml) were added thereto, and the reaction mixture was agitated for one hour at 140° C. The reaction mixture was naturally cooled to room temperature, and then was filtered, and the filtrate was concentrated under reduced pressure. The concentration residue was poured into water and agitated for a while, and then a solid that precipitated was collected by filtration and dried under reduced pressure. As a result, 160.03 g (yield: 76%) of the indicated compound was obtained.

Workup

  1. customequipped with a stirrer under a nitrogen gas stream
  2. stirringthe reaction mixture was agitated for one hour at 140° C
  3. temperatureThe reaction mixture was naturally cooled to room temperature
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionThe concentration residue was poured into water
  7. stirringagitated for a while
  8. customa solid that precipitated
  9. filtrationwas collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-d535d313462c473fb3c97ccbb03a212b
Source dataset
uspto-grants-2016_07
Patent number
US09394240B2

Reaction notes

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