Ethyl Acetate → 5-Chloro-4'-fluorobiphenyl-2-amine

HRID 238957ノート

反応式

HRID 238957 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH:7]=1.[Cl-].[NH4+].C(OCC)(=O)C>C(O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 674497455-Chloro-4'-fluoro-2-nitrobiphenyl

生成物 1

HCID 584829885-Chloro-4'-fluorobiphenyl-2-amine収率 70.1%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To a solution of the above 5-chloro-4′-fluoro-2-nitrobiphenyl (4.20 g, 15.7 mmol) and iron powder (2.75 g, 49.3 mmol) in ethanol (20 mL), a saturated aqueous ammonium chloride solution (aq., 8.0 mL) was added, and the mixture was stirred at 90° C. for 30 minutes. After the reaction, the reaction mixture was cooled to room temperature and ethyl acetate (30 mL) was added. After the organic phase was washed with water (30 mL), it was dried with sodium sulfate. After the filtration and concentration, the residue was purified by silica gel column chromatography (ethyl acetate/hexane, 1:20-1:3, v/v) to give the title compound (2.43 g, 11.0 mmol, 67%).

後処理

  1. customAfter the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. washAfter the organic phase was washed with water (30 mL), it
  4. dry with materialwas dried with sodium sulfate
  5. filtrationAfter the filtration and concentration
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane, 1:20-1:3

出典と根拠

ORDレコード
ord-40d71a0d48274ca1b68444f92e9bd1e1
出典データセット
uspto-grants-2014_02
特許番号
US08642640B2

反応ノート

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