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

HRID 2405155노트

반응식

HRID 2405155 반응식
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]

참가 물질

5

반응물 2

HCID 124951-Iodo-4-nitrobenzene2회HCID 69585Ethyl bromodifluoroacetate

생성물 1

HCID 10586437Ethyl 2,2-difluoro-2-(4-nitrophenyl)acetate

시약·촉매·용매 2

HCID 23978Copper촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
55 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-6d8ed6f762a249c490a667c1517de75c
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802886B2

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