Hydrochloric Acid → HCID 12585549, compound

HRID 2405153Notes

Reaction equation

HRID 2405153 reaction equation
C([O:3][C:4](=[O:20])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)([F:7])[F:6])C.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[C:11]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:12]=[CH:13][C:8]([C:5]([F:6])([F:7])[C:4]([OH:20])=[O:3])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12585539HCID 12585539, compound2×

Product 1

HCID 12585549HCID 12585549, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the above-described scheme, 2-(biphenyl-4-yl)-2,2-difluoroacetic acid ethyl ester (Compound 2g; 82.9 mg, 0.3 mmol), 1N K2CO3 solution (0.9 mL) and DMF (0.9 mL) were put into an eggplant flask, and the mixture was stirred at room temperature 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-(biphenyl-4-yl)-2,2-difluoroacetic acid (Compound 4g) was obtained with a yield of 88%.

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-5d8cdf2f56e641ffaa4c04502f4ef325
Source dataset
uspto-grants-2014_08
Patent number
US08802886B2

Reaction notes

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