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Acetic Acid → 4-Bromo-5-(2,4-difluorophenoxy)benzene-1,2-diamine

HRID 629294
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HRID 629294 반응식
[Br:1][C:2]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])=[CH:7][C:5]([NH2:6])=[C:4]([N+:18]([O-])=O)[CH:3]=1.C(O)(=O)C>O1CCCC1.C(OCC)(=O)C.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([NH2:6])=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]
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참가 물질

6

반응물 2

HCID 176Acetic AcidHCID 1180936684-Bromo-5-(2,4-difluorophenoxy)-2-nitroaniline

생성물 1

HCID 1180936764-Bromo-5-(2,4-difluorophenoxy)benzene-1,2-diamine수율 99.8%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate
용매

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온도
60 °C

실험 절차

A suspension of 4-bromo-5-(2,4-difluorophenoxy)-2-nitroaniline (0.406 g, 1.18 mmol) in tetrahydrofuran (5.0 mL) was treated with iron (0.657 g, 11.8 mmol), followed by acetic acid (4.9 mL, 87 mmol) and stirred at 60° C. for 1 h. The reaction mixture was diluted with ethyl acetate and quenched carefully with saturated sodium bicarbonate. The organic layer was separated and washed again with saturated sodium bicarbonate and brine, dried with magnesium sulfate, filtered, and concentrated to give the desired product (371 mg, quantitative) that was used immediately without further purification. LCMS calculated for C12H10BrF2N2O (M+H)+: m/z=315.0, 317.0. found: 315.0, 316.9.

후처리

  1. customquenched carefully with saturated sodium bicarbonate
  2. customThe organic layer was separated
  3. washwashed again with saturated sodium bicarbonate and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-26b489fef1bc4ac395a040371148d955
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09315501B2

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