Ammonium Chloride → 3-Bromo-5-(difluoromethyl)aniline

HRID 1040031ノート

反応式

HRID 1040031 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH:11]([F:13])[F:12])[CH:3]=1.[NH4+].[Cl-]>C(O)C.O.C(OCC)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH:11]([F:12])[F:13])[CH:3]=1)[NH2:8]

参加物

7

反応物 2

HCID 25517Ammonium ChlorideHCID 672481711-Bromo-3-(difluoromethyl)-5-nitrobenzene

生成物 1

HCID 584563863-Bromo-5-(difluoromethyl)aniline収率 82.1%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

Iron (1.99 g, 35.7 mmol) was added to a vigorously stirred mixture of 1-bromo-3-(difluoromethyl)-5-nitrobenzene (1.80 g, 7.14 mmol) and NH4Cl (0.191 g, 3.57 mmol) in ethanol (30 mL) and water (15 mL). The mixture was heated to 95° C. for 2 h. It was then diluted with ethyl acetate while still hot and filtered over Celite. The filtrate was washed with dilute aqueous NaHCO3 and brine. After solvent evaporation the residue was purified through a silica plug, eluting with 1:5 ethyl acetate:hexanes to yield 3-bromo-5-(difluoromethyl)aniline (1.3 g, 5.86 mmol, 82%).

後処理

  1. filtrationfiltered over Celite
  2. washThe filtrate was washed with dilute aqueous NaHCO3 and brine
  3. customAfter solvent evaporation the residue
  4. customwas purified through a silica plug
  5. washeluting with 1:5 ethyl acetate

出典と根拠

ORDレコード
ord-42645d21227d45138c896c2aef8ff410
出典データセット
uspto-grants-2013_10
特許番号
US08551984B2

反応ノート

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