Hydrochloric Acid → 2,2-Difluoro-2-(4-nitrophenyl)acetic acid

HRID 2405148Notes

Reaction equation

HRID 2405148 reaction equation
C([O:3][C:4](=[O:17])[C:5]([F:16])([F:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)C.[OH-].[Na+].Cl>>[F:15][C:5]([F:16])([C:6]1[CH:7]=[CH:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1)[C:4]([OH:17])=[O:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10586437Ethyl 2,2-difluoro-2-(4-nitrophenyl)acetate2×

Product 1

HCID 467392012,2-Difluoro-2-(4-nitrophenyl)acetic acid

Procedure

According to the above-described scheme, 2,2-difluoro-2-(4-nitrophenyl)acetic acid ethyl ester (Compound 2b; 147 mg, 0.6 mmol) and 1N NaOH solution (3 mL) were put into an eggplant flask, and the mixture was stirred at room temperature for 19 hours. After the reaction, the reaction mixture was neutralized with 5% HCl solution, extracted with ethyl acetate and washed with water, and an organic layer was dried with anhydrous sodium sulfate. Ethyl acetate was distilled away under reduced pressure, and by carrying out purification by silica gel column chromatography, 2,2-difluoro-2-(4-nitrophenyl)acetic acid (Compound 4b) was obtained with a yield of 93%.

Workup

  1. customwere put into an eggplant flask
  2. customAfter the reaction
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialan organic layer was dried with anhydrous sodium sulfate
  6. distillationEthyl acetate was distilled away under reduced pressure
  7. custompurification by silica gel column chromatography

Sources & evidence

ORD record
ord-bc06145d78254742b44bde12445ab5ad
Source dataset
uspto-grants-2014_08
Patent number
US08802886B2

Reaction notes

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