Water → 4-Bromo-3,5-difluoro-2-iodoaniline

HRID 1054618

반응식

HRID 1054618 반응식
[Br:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:10].C1C(=O)N([I:18])C(=O)C1.O>C(O)(=O)C>[Br:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([I:18])[C:3]=1[F:10]

참가 물질

5

반응물 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 27362604-Bromo-3,5-difluoroaniline

생성물 1

HCID 866986224-Bromo-3,5-difluoro-2-iodoaniline수율 109.9%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of the 4-bromo-3,5-difluoroaniline (5 g, 20 mmol) in acetic acid (60 mL) was added NIS (5.68 g). The reaction mixture was stirred at room temperature for two hours, and poured into water (300 mL). The product was extracted with ethyl acetate (2×200 mL), and the combined organic layers were washed with 1 N aqueous NaOH (200 mL) and saturated aqueous sodium thiosulfate (100 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The oily residue was filtered through a plug of silica gel, eluting with heptane/ethyl acetate (4:1). The filtrate was concentrated in vacuo to give the title compound (7.34 g) as a white solid. 1H NMR (500 MHz, CDCl3) δ 6.44 (dd, J=10.00, 1.95 Hz, 1 H) 4.46 (br. s., 2 H).

후처리

  1. extractionThe product was extracted with ethyl acetate (2×200 mL)
  2. washthe combined organic layers were washed with 1 N aqueous NaOH (200 mL) and saturated aqueous sodium thiosulfate (100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationThe oily residue was filtered through a plug of silica gel
  7. washeluting with heptane/ethyl acetate (4:1)
  8. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-f8ae1e31448d47b58242079303745cb4
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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