Acetic Acid → 3-Fluoro-4-(methylsulfonyl)aniline

HRID 396767ノート

反応式

HRID 396767 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N+:12]([O-])=O)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(O)(=O)C>O.[Fe]>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9])[NH2:12]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 223167812-Fluoro-1-(methylsulfonyl)-4-nitrobenzene

生成物 1

HCID 223166093-Fluoro-4-(methylsulfonyl)aniline収率 90%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
95 °C

実験手順

A mixture of 3-fluoro-4-(methylsulfonyl)nitrobenzene (8 g, 36.5 mmol), iron powder (22 g, 394 mmol), and acetic acid (0.3 mL) in water (200 mL) was heated at 95° C. for 3 hours. After cooling, insolubles were filtered off by Celite. The filtrate was extracted with ethyl acetate (200 mL×2), the combined organic layer washed with water, brine, dried over MgSO4, and concentrated in vacuo. Chromatographic purification of the residue eluting with ethyl acetate/hexane (1/1) provided the subtitle compound (6.2 g, 90% yield).

後処理

  1. temperatureAfter cooling
  2. filtrationinsolubles were filtered off by Celite
  3. extractionThe filtrate was extracted with ethyl acetate (200 mL×2)
  4. washthe combined organic layer washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification of the residue
  8. washeluting with ethyl acetate/hexane (1/1)

出典と根拠

ORDレコード
ord-ad14a11c528642279f3d894b74184ebc
出典データセット
uspto-grants-2003_08
特許番号
US06608095B2

反応ノート

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