Hydrochloric Acid → 4-Bromo-1-chloro-2-iodobenzene

HRID 72270

반응식

HRID 72270 반응식
N(OC(C)(C)C)=O.[Br:8][C:9]1[CH:15]=[CH:14][C:12](N)=[C:11]([I:16])[CH:10]=1.[ClH:17]>C(#N)C.[Cu](Cl)Cl>[Br:8][C:9]1[CH:15]=[CH:14][C:12]([Cl:17])=[C:11]([I:16])[CH:10]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 8239344-Bromo-2-iodoaniline

생성물 1

HCID 510000714-Bromo-1-chloro-2-iodobenzene

시약·촉매·용매 2

HCID 24014Cupric Chloride촉매HCID 6342Acetonitrile용매2회

반응 조건

온도
60 °C

실험 절차

tert-Butyl nitrite (11.1 ml, 93.3 mmol) is added to a suspension of copper(II) chloride (10.04 g, 75 mmol) in acetonitrile (224 ml) and the mixture is heated with stirring to 60° C. A solution of 4-bromo-2-iodoaniline (18.54 g, 62 mmol) in acetonitrile (56 ml) is added dropwise over about an hour, and once the addition is complete the mixture is stirred at 60° C. for 2 hours. The mixture is cooled to room temperature, poured into 20% aqueous hydrochloric acid (1.3 liters) and extracted with diethyl ether (1.5 liters). The organic extract is separated and the aqueous re-extracted with ether (1 liter). The organic extracts are combined and dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel to give 4-bromo-1-chloro-2-iodobenzene (8.62 g) as an oil.

후처리

  1. temperaturethe mixture is heated
  2. additiononce the addition
  3. stirringis stirred at 60° C. for 2 hours
  4. temperatureThe mixture is cooled to room temperature
  5. extractionextracted with diethyl ether (1.5 liters)
  6. extractionThe organic extract
  7. customis separated
  8. extractionthe aqueous re-extracted with ether (1 liter)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customthe filtrate evaporated in vacuo
  12. customThe residue is further purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-4e2037945de5411f9f7f8ce565c4f85c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828908B2

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