Ethyl Acetate → 2-Bromo-5-fluoro-4-nitroaniline

HRID 575994

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HRID 575994 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[NH2:5].C(OCC)(=O)C.[Br:18]N1C(=O)CCC1=O>CS(C)=O>[Br:18][C:6]1[CH:7]=[C:8]([N+:9]([O-:11])=[O:10])[C:2]([F:1])=[CH:3][C:4]=1[NH2:5]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 754013-Fluoro-4-nitroaniline

생성물 1

HCID 574885132-Bromo-5-fluoro-4-nitroaniline수율 50%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
22 °C

실험 절차

A flask was charged with 3-fluoro-4-nitroaniline (1.0 equiv) followed by ethyl acetate (10 vol) and stirred to dissolve all solids. N-Bromosuccinimide (1.0 equiv) was added as a portion-wise as to maintain internal temperature of 22° C. At the end of the reaction, the reaction mixture was concentrated in vacuo on a rotavap. The residue was slurried in distilled water (5 vol) to dissolve and remove succinimide. (The succinimide can also be removed by water workup procedure.) The water was decanted and the solid was slurried in 2-propanol (5 vol) overnight. The resulting slurry was filtered and the wetcake was washed with 2-propanol, dried in vacuum oven at 50° C. overnight with N2 bleed until constant weight was achieved. A yellowish tan solid was isolated (50% yield, 97.5% AUC). Other impurities were a bromo-regioisomer (1.4% AUC) and a di-bromo adduct (1.1% AUC). 1H NMR (500 MHz, DMSO)

후처리

  1. dissolutionto dissolve all solids
  2. customAt the end of the reaction
  3. concentrationthe reaction mixture was concentrated in vacuo on a rotavap
  4. dissolutionto dissolve
  5. customremove succinimide
  6. custom(The succinimide can also be removed by water workup procedure
  7. custom) The water was decanted
  8. filtrationThe resulting slurry was filtered
  9. washthe wetcake was washed with 2-propanol
  10. dry with materialdried in vacuum oven at 50° C. overnight with N2
  11. customA yellowish tan solid was isolated (50% yield, 97.5% AUC)

출처 및 근거

ORD 기록
ord-ffd44fb689384bbbaebea332048aa6b4
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09035072B2

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