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Sulfuric Acid → 4-(4-Bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1072507
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반응식

HRID 1072507 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH3:11])=[CH:4][CH:3]=1.OS(O)(=O)=O.[OH-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:18]3[C:13](=[C:14]([Cl:20])[CH:15]=[C:16]([Cl:19])[CH:17]=3)[CH2:12][N:10]([CH3:11])[CH2:9]2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 223868482-((2,4-Dichlorobenzyl)(methyl)amino)-1-(4-bromophenyl)ethanol

생성물 1

HCID 101772114-(4-Bromophenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline수율 50%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

5.45 g (14.0 mmol) of 1-(4-bromo-phenyl)-2-[(2,4-dichloro-benzyl)-methyl-amino]-ethanol was introduced into 15 ml of dichloromethane and, at 0° C., 15 ml of conc. H2SO4 are added. After stirring at room temperature for 2 hours, the reaction mixture was poured onto ice and made alkaline with 6 N NaOH. Three extractions with dichloromethane were carried out. The combined organic phases were dried with MgSO4 and concentrated. For further purification, the residue was chromatographed on silica gel, resulting in 2.6 g of the title compound as a yellowish oil. 4-(4-Bromo-phenyl)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinoline, Hydrochloride;

후처리

  1. additionthe reaction mixture was poured onto ice
  2. extractionThree extractions with dichloromethane
  3. dry with materialThe combined organic phases were dried with MgSO4
  4. concentrationconcentrated
  5. customFor further purification
  6. customthe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-e8bff8e7970649649270640a359d5372
출처 데이터셋
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06911453B2

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