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

HRID 1036857

反応式

HRID 1036857 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-09c2f1c3d63145a3be379713e6a58b08
出典データセット
uspto-grants-2013_10
特許番号
US08546427B2

関連ノート

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