Hydrochloric Acid → HCID 55270836, compound

HRID 2405147Notes

Reaction equation

HRID 2405147 reaction equation
C([O:3][C:4](=[O:16])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=1)([F:7])[F:6])C.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[C:14]([C:11]1[CH:10]=[CH:9][C:8]([C:5]([F:6])([F:7])[C:4]([OH:16])=[O:3])=[CH:13][CH:12]=1)#[N:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66913596HCID 66913596, compound2×

Product 1

HCID 55270836HCID 55270836, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

According to the above-described scheme, 2-(4-cyanophenyl)-2,2-difluoroacetic acid ethyl ester (Compound 2a; 202.7 mg, 0.9 mmol), 1N K2CO3 solution (2.7 mL) and DMF (2.7 mL) were put into an eggplant flask, and the mixture was stirred at 25° C. for 18 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-(4-cyanophenyl)-2,2-difluoroacetic acid (Compound 4a) was obtained with a yield of 79%.

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-6e4a4ca0324147afac0a07273120a607
Source dataset
uspto-grants-2014_08
Patent number
US08802886B2

Reaction notes

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