4-Iodobiphenyl → HCID 12585539, compound

HRID 2405160Notes

Reaction equation

HRID 2405160 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:14]([O:16][C:17](=[O:22])[C:18](Br)([F:20])[F:19])[CH3:15]>[Cu].CS(C)=O>[CH2:14]([O:16][C:17](=[O:22])[C:18]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)([F:20])[F:19])[CH3:15]

Participants

5

Reactant 2

HCID 153224-Iodobiphenyl2×HCID 69585Ethyl bromodifluoroacetate

Product 1

HCID 12585539HCID 12585539, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

According to the Kumadaki method (supra) and the above-described scheme, 4-iodobiphenyl (Compound 1g; 840.3 mg, 3.0 mmol), bromodifluoroacetic acid ethyl ester (609.0 mg, 3.0 mmol), copper powder (381.0 mg, 6.0 mmol) and DMSO (6.0 mL) were put into a two-neck reaction tube, and the mixture was stirred under argon atmosphere at 55° C. for 24 hours. The reaction mixture was 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 ethyl ester (Compound 2g) was obtained with a yield of 65%.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialan organic layer was dried with anhydrous sodium sulfate
  4. distillationEthyl acetate was distilled away under reduced pressure
  5. custompurification by silica gel column chromatography

Sources & evidence

ORD record
ord-0f74253bc9954b1d8e2d3b5dfaa3bdff
Source dataset
uspto-grants-2014_08
Patent number
US08802886B2

Reaction notes

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