4-Chloroaniline → 2-(3-Bromophenyl)-6-chloro-4,4-dimethyl-1,2,3,4-tetrahydroquinoline

HRID 1036857노트

반응식

HRID 1036857 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O.[CH2:18]=[C:19]([CH3:21])[CH3:20].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C(#N)C.C(OCC)(=O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[CH2:18][C:19]([CH3:21])([CH3:20])[C:6]3[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:7]=3)[NH:8]2)[CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 4

HCID 78124-ChloroanilineHCID 8255IsobutyleneHCID 765833-BromobenzaldehydeHCID 2733225Ytterbium triflate

생성물 1

HCID 672912592-(3-Bromophenyl)-6-chloro-4,4-dimethyl-1,2,3,4-tetrahydroquinoline수율 40%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

To a stirred solution of 4-chlorophenylamine (10.0 g, 78.4 mmol) and 3-bromobenzaldehyde (9.2 mL, 78.4 mmol) in acetonitrile (150 mL) were added isobutene (21.0 mL, 313.5 mmol) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (5.8 g, 9.5 mmol). The resulting mixture was stirred at 85° C. for 18 h in sealed tube. The mixture was diluted with ethyl acetate (300 mL) and washed with water (100 mL×2) and brine (100 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 0-10% ethyl acetate in petroleum ether) to afford 2-(3-bromo-phenyl)-6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline (11.0 g, 40.0%) as a light yellow solid: LC/MS m/e obsd. (ESI+) [(M+H)+] 350.0 & 352.0.

후처리

  1. washwashed with water (100 mL×2) and brine (100 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by ISCO combi-flash chromatography (gradient elution, 0-10% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-09c2f1c3d63145a3be379713e6a58b08
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546427B2

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