Ammonium Chloride → 3-Amino-5-bromo-4-chlorobenzonitrile

HRID 1430777

反応式

HRID 1430777 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-])=O)[C:9]=1[Cl:10])[C:5]#[N:6].[Cl-].[NH4+]>C1COCC1.CO.O.[Fe]>[NH2:11][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([Br:1])[C:9]=1[Cl:10])[C:5]#[N:6]

参加物

7

反応物 2

HCID 25517Ammonium Chloride2 回HCID 867084553-Bromo-4-chloro-5-nitrobenzonitrile

生成物 1

HCID 867084563-Amino-5-bromo-4-chlorobenzonitrile収率 100.3%

試薬・触媒・溶媒 4

HCID 23925Iron触媒2 回HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

(I1D): A mixture of 3-bromo-4-chloro-5-nitrobenzonitrile (0.99 g, 3.79 mmol), iron (1.057 g, 18.93 mmol) and ammonium chloride (2.025 g, 37.9 mmol) in THF, MeOH and water (60 ml, 1:1:1) was heated to reflux for 1 h. More iron (0.5 g) and NH4Cl (2 g) added, heated for another 2 h and then cooled to RT. Filtered off solid, the filtrate was concentrated to remove the organic solvent. The residue was diluted with water, extracted with EtOAc twice, dried and concentrated to dryness. The resulting solid was trituard with EtOAc, solid was filtered off through celite pad and the filtrate was concentrated to give 0.88 g of 3-amino-5-bromo-4-chlorobenzonitrile as yellow solid which was used as such in the next reaction.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. temperatureheated for another 2 h
  4. filtrationFiltered off solid
  5. concentrationthe filtrate was concentrated
  6. customto remove the organic solvent
  7. additionThe residue was diluted with water
  8. extractionextracted with EtOAc twice
  9. customdried
  10. concentrationconcentrated to dryness
  11. filtrationwas filtered off through celite pad
  12. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-0d765f96ef6a4bd388351a7c7e3da6cc
出典データセット
uspto-grants-2015_01
特許番号
US08940736B2

関連ノート

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