Chlorosuccinimide → 2-Amino-3-chloro-5-fluorobenzonitrile

HRID 626780ノート

反応式

HRID 626780 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C:4]#[N:5].[Cl:11]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:9]([Cl:11])=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[C:4]#[N:5]

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 27377042-Amino-5-fluorobenzonitrile

生成物 1

HCID 668017282-Amino-3-chloro-5-fluorobenzonitrile収率 51.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-amino-5-fluorobenzonitrile (15.0 g, 110 mmol) in anhydrous acetonitrile (300 mL) was added N-chlorosuccinimide (16.0 g, 120 mmol) portionwise. The reaction mixture was heated at 80° C. for 18 hours under nitrogen. The resultant mixture was allowed to cool, concentrated under reduced pressure and then partitioned between EtOAc and water. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel flash chromatography (10-20% diethyl ether in pentane) to afford the title compound as an off-white solid (9.6 g, 51% yield). 1H NMR (300 MHz, CDCl3): δ 7.27 (dd, J=7.9, 2.9 Hz, 1H), 7.08 (dd, J=7.6, 2.9 Hz, 1H), 4.67 (br s, 2H).

後処理

  1. temperatureto cool
  2. concentrationconcentrated under reduced pressure
  3. custompartitioned between EtOAc and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. customthe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by silica gel flash chromatography (10-20% diethyl ether in pentane)

出典と根拠

ORDレコード
ord-447a0268d635451a9f75668571e1900b
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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