1-Iodo-4-nitrobenzene → Ethyl 2,2-difluoro-2-(4-nitrophenyl)acetate

HRID 2405155Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[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][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)[CH3:12]

Participants

Conditions

Temperature: 55 °C

Procedure

According to the Kumadaki method (supra) and the above-described scheme, 4-iodonitrobenzene (Compound 1b; 249.0 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-(4-nitrophenyl)acetic acid ethyl ester (Compound 2b) was obtained with a yield of 58%.

Workup

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

Sources & evidence

ORD record: ord-6d8ed6f762a249c490a667c1517de75c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802886B2

Reaction notes

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