Hydrochloric Acid → 2-Bromo-4-chloro-1-(1-methylethyl)benzene

HRID 59586

반응식

HRID 59586 반응식
[ClH:1].[Br:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11])N.N([O-])=O.[Na+]>O.[Cu]Cl.S(N)(=O)(=O)O>[Br:2][C:3]1[CH:4]=[C:5]([Cl:1])[CH:7]=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11]

참가 물질

7

반응물 3

HCID 313Hydrochloric Acid2회HCID 2807993-Bromo-4-isopropylanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 679882822-Bromo-4-chloro-1-(1-methylethyl)benzene수율 62.3%

시약·촉매·용매 3

HCID 5987Sulfamic Acid촉매HCID 62652Cuprous chloride촉매HCID 962Water용매3회

반응 조건

온도
5 °C

실험 절차

Hydrochloric acid (152 g, 31% strength, 1.29 mol) was added dropwise to a suspension of 3-bromo-4-isopropylaniline (VII) (100 g, 0.43 mol) and water (150 g) at room temperature. The suspension was subsequently cooled to 5° C. and a solution of sodium nitrite (32.7 g, 0.46 mol) in water (140 g) was added dropwise over a period of 2 hours. After stirring for another 1 hour, amidosulphuric acid (2.5 g, 0.026 mol) was added. Copper(I) chloride (10.8 g, 0.11 mol), hydrochloric acid (202 g, 31%, 1.72 mol) and water (75 g) were placed in a second flask and the diazonium salt generated previously was added dropwise over a period of 30 minutes. After stirring for another 1.5 hours, the mixture was extracted with dichloromethane (250 g), the phases were separated and dichloromethane was distilled off under reduced pressure. The crude product obtained was purified by distillation. 2-Bromo-4-chloro-1-isopropylbenzene (62.6 g, 94.8 GC-% by area. 59% of theory) was obtained as a colourless oil.

후처리

  1. stirringAfter stirring for another 1.5 hours
  2. extractionthe mixture was extracted with dichloromethane (250 g)
  3. customthe phases were separated
  4. distillationdichloromethane was distilled off under reduced pressure
  5. customThe crude product obtained
  6. distillationwas purified by distillation

출처 및 근거

ORD 기록
ord-75e5646be5c9480fba177cf39bd72a36
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440908B2

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