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Ethyl Acetate → 2-Chloro-4-nitro-6-(trifluoromethyl)aniline

HRID 905576
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HRID 905576 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1)([O-:3])=[O:2].[Cl:15]N1C(=O)CCC1=O.C(OCC)(=O)C>C(#N)C>[Cl:15][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]([C:11]([F:12])([F:13])[F:14])[C:7]=1[NH2:10]
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참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 671284-Nitro-alpha,alpha,alpha-trifluoro-o-toluidine

생성물 1

HCID 137844272-Chloro-4-nitro-6-(trifluoromethyl)aniline수율 75%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
150 °C

실험 절차

4-Nitro-2-trifluoromethyl-phenylamine (5.6 g) and N-chlorosuccinimide (4.0 g) were suspended in acetonitrile (15 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. Ethyl acetate (80 mL) was added and the organic phase was washed with 5% aqueous NaOH (2×50 mL), water (2×50 mL) and brine (2×50 mL). The organic phase was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 4.9 g (75% yield) of the title compound as a yellow solid. 1H NMR (500 MHz, CDCl3): 5.35 (b, 2H), 8.35 (b, 1H), 8.37 (b, 1H).

후처리

  1. washthe organic phase was washed with 5% aqueous NaOH (2×50 mL), water (2×50 mL) and brine (2×50 mL)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-4ab29f4f687a457cac3605ebd4c4b892
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08012962B2

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