Ethyl Acetate → 2,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline

HRID 240959

반응식

HRID 240959 반응식
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].F[C:21]1[C:26]([F:27])=[C:25]([F:28])[CH:24]=[C:23]([F:29])[C:22]=1[N+:30]([O-:32])=[O:31].C(OCC)(=O)C>C1COCC1>[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:21]1[C:22]([N+:30]([O-:32])=[O:31])=[C:23]([F:29])[CH:24]=[C:25]([F:28])[C:26]=1[F:27]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 675661,2,3,5-Tetrafluoro-4-nitrobenzeneHCID 1856942-Fluoro-4-iodoanilineHCID 2733832Lithium Hexamethyldisilazide2회

생성물 1

HCID 574300722,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline수율 59.24%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A stirred solution of 2-fluoro-4-iodoaniline (3.64 gm, 15.37 mmol) in dry THF (100 ml) under nitrogen was cooled to −78° C. and a solution of 1.0 M lithium hexa methyl disilazide (LiN(SiMe3)2) “LHMDS” (15.37 ml, 15.37 mmol) was added slowly. This reaction mixture was kept stirring at −78° C. for another hour and then 2,3,4,6-tetrafluoronitrobenzene was added. The reaction mixture was allowed to warm to room temperature and stirring continued for another 16 hours. Ethyl acetate (200 ml) was added to the reaction mixture and was washed with water. Organic layer was dried over sodium sulfate and further purified by column chromatography to provide yellow solid (3.75 gm, yield: 59.24%). M−H+: 410.9. 1H NMR (DMSO, 300 MHz): 6.85 (t, 1H); 7.38 (d, 1H); 7.62 (m, 2H); 8.78 (s, 1H).

후처리

  1. temperatureto warm to room temperature
  2. stirringstirring
  3. washwas washed with water
  4. dry with materialOrganic layer was dried over sodium sulfate
  5. customfurther purified by column chromatography

출처 및 근거

ORD 기록
ord-d3001c237f7e4fb6a70b29de9dd72c68
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648116B2

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