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

HRID 629294
ノート
印刷プレビュー

反応式

HRID 629294 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate
溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-26b489fef1bc4ac395a040371148d955
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09315501B2

反応ノート

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