Water → Methyl 4-chloro-5-nitro-2-(trifluoromethyl)benzoate

HRID 1942496Notes

Reaction equation

HRID 1942496 reaction equation
O[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=1.P(Cl)(Cl)([Cl:21])=O.O>CN(C)C=O>[Cl:21][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 58376066Methyl 4-hydroxy-5-nitro-2-(trifluoromethyl)benzoate

Product 1

HCID 58376260Methyl 4-chloro-5-nitro-2-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 4-hydroxy-5-nitro-2-(trifluoromethyl)benzoate (15 g) in dimethyl-formamide (170 ml) was added dropwise phosphorus oxychloride (7.4 ml) under ice-cooling. The reaction solution was heated at 100° C., and stirred for 2 hours. After the reaction was complete, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give methyl 4-chloro-5-nitro-2-(trifluoromethyl)benzoate (14.78 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-20193d9ccd6d4929b7288ee95deb65d2
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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