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

HRID 2405155ノート

反応式

HRID 2405155 の反応式
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]

参加物

5

反応物 2

HCID 124951-Iodo-4-nitrobenzene2 回HCID 69585Ethyl bromodifluoroacetate

生成物 1

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

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
55 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-6d8ed6f762a249c490a667c1517de75c
出典データセット
uspto-grants-2014_08
特許番号
US08802886B2

反応ノート

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