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

HRID 1430777

반응식

HRID 1430777 반응식
[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]

참가 물질

7

반응물 2

HCID 25517Ammonium Chloride2회HCID 867084553-Bromo-4-chloro-5-nitrobenzonitrile

생성물 1

HCID 867084563-Amino-5-bromo-4-chlorobenzonitrile수율 100.3%

시약·촉매·용매 4

HCID 23925Iron촉매2회HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-0d765f96ef6a4bd388351a7c7e3da6cc
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940736B2

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