Sodium Hydroxide → HCID 86665743, compound

HRID 1191656Notes

Reaction equation

HRID 1191656 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].Cl[C:14]([F:19])([F:18])C([O-])=O.[Na+].[OH-].[Na+]>CN(C)C=O.O>[F:18][CH:14]([F:19])[O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 392115-Hydroxy-2-nitrobenzaldehydeHCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 86665743HCID 86665743, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 5-hydroxy-2-nitrobenzaldehyde (500 mg) in N,N-dimethylformamide (4.3 mL) were added sodium chlorodifluoroacetate (456 mg), sodium hydroxide (120 mg) and water (0.060 mL) at room temperature, and the mixture was stirred at 125° C. for one hour. The reaction mixture was cooled to room temperature, diluted with water and then extracted with ethyl acetate. The organic layer was washed successively with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (240 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with water and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-616dd4b1d26e4040bb51816ac47f9b16
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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