Ethyl Acetate → 1383974-37-5

HRID 2278657Notes

Reaction equation

HRID 2278657 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].Cl[C:13]([F:18])([F:17])C([O-])=O.[Na+].[C:20](=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[F:17][CH:13]([F:18])[O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:2]=1[CH2:1][CH2:20][NH:8]2

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 795792-Methyl-3-nitrophenolHCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 866992831383974-37-5

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
110 °C

Procedure

A solution of 10 g of 2-methyl-3-nitrophenol in 20 ml of N,N-dimethylformamide is added to a mixture of 23.4 g of sodium chlorodifluoroacetate and 22 g of potassium carbonate in 30 ml of N,N-dimethylformamide and 6 ml of water. The reaction mixture is then heated at 110° C. for 3 hours and left to stand for 16 hours, and then treated with a mixture of water and ethyl acetate. The organic phase is washed with 1N sodium hydroxide, water and a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure, so as to give the expected product in the form of a brown oil, used as it is in the next step.

Workup

  1. waitleft
  2. washThe organic phase is washed with 1N sodium hydroxide, water
  3. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db833892bcb44212b36e7746d38f582b
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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