o-Iodonitrobenzene → HCID 68193918, compound

HRID 2405156Notes

Reaction equation

HRID 2405156 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([O:13][C:14](=[O:19])[C:15](Br)([F:17])[F:16])[CH3:12]>[Cu].CS(C)=O>[CH2:11]([O:13][C:14](=[O:19])[C:15]([F:17])([F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[CH3:12]

Participants

5

Reactant 2

HCID 69115o-Iodonitrobenzene2×HCID 69585Ethyl bromodifluoroacetate

Product 1

HCID 68193918HCID 68193918, 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, 2-iodonitrobenzene (Compound 1c; 250.0 mg, 1.0 mmol), bromodifluoroacetic acid ethyl ester (203 mg, 1.0 mmol), copper powder (128 mg, 2.0 mmol) and DMSO (2.0 mL) were put into a two-neck reaction tube, and the mixture was stirred under argon atmosphere at 55° C. for 15 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, 2,2-difluoro-2-(2-nitrophenyl)acetic acid ethyl ester (Compound 2c) was obtained with a yield of 13%.

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-77cd2b658a0149ec826937dca2192bec
Source dataset
uspto-grants-2014_08
Patent number
US08802886B2

Reaction notes

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