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

HRID 59586

反応式

HRID 59586 の反応式
[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]

参加物

7

反応物 3

HCID 313Hydrochloric Acid2 回HCID 2807993-Bromo-4-isopropylanilineHCID 23668193Sodium Nitrite

生成物 1

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

試薬・触媒・溶媒 3

HCID 5987Sulfamic Acid触媒HCID 62652Cuprous chloride触媒HCID 962Water溶媒3 回

反応条件

温度
5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-75e5646be5c9480fba177cf39bd72a36
出典データセット
uspto-grants-2016_09
特許番号
US09440908B2

関連ノート

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