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

HRID 240983

반응식

HRID 240983 반응식
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[F:11][C:12]1[CH:18]=[C:17]([I:19])[CH:16]=[CH:15][C:13]=1[NH2:14].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:11][C:12]1[CH:18]=[C:17]([I:19])[CH:16]=[CH:15][C:13]=1[NH:14][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

실험 절차

A solution of 1.0 M lithium hexa methyl disilazide (LiN(SiMe3)2) “LHMDS” (15.37 mL, 15.37 mmol) was slowly added to a stirred solution of 2-fluoro-4-iodoaniline (3.64 g, 15.37 mmol) in dry THF (100 mL) under nitrogen at −78° C. and stirring continued at −78° C. for another hour. 2,3,4,6-Tetrafluoronitrobenzene was added, and the reaction mixture was allowed to warm to room temperature and stirring continued for another 16 hours. Ethyl acetate (200 mL) was added and the organic phase was washed with water, dried over sodium sulfate and further purified by column chromatography to provide the product as a yellow solid (3.75 g, 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. waitcontinued at −78° C. for another hour
  2. stirringstirring
  3. washthe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. customfurther purified by column chromatography

출처 및 근거

ORD 기록
ord-c28b96badc7144d894fbe9bcfebeefb5
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648116B2

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