Toluene → 6-Bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline

HRID 928796ノート

反応式

HRID 928796 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[C:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=[C:5]2[Cl:24].C1(C)C=CC=CC=1.[CH3:32][O-:33].[Na+].[Al]>CCCCCC.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:33][CH3:32])[C:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=[C:5]2[Cl:24]

参加物

6

反応物 4

HCID 1140TolueneHCID 5359268AluminumHCID 10942334Sodium MethoxideHCID 867156286-Bromo-2,4-dichloro-3-(4-(trifluoromethyl)benzyl)quinoline2 回

生成物 1

HCID 867156276-Bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline

試薬・触媒・溶媒 1

HCID 21226440Methylenechloride Hexane溶媒

反応条件

温度
80 °C

実験手順

To a 1 L flask containing 6-bromo-2,4-dichloro-3-(4-(trifluoromethyl)benzyl)quinoline (32.5 g, 74.7 mmol, Intermediate 47: step c) was added toluene (550 mL) followed by solid sodium methoxide (40 g, 740 mmol, 97% purity) at room temperature. The suspension was stirred at reflux (˜118° C.) in an aluminum mantle. TLC (50% Hexane-DCM) and HPLC after 5.5 hours showed the reaction to be complete. The reaction mixture was filtered through Celite® while still warm (˜80° C.) and rinsed with warm toluene (˜70° C., 500 mL). The colorless filtrate was concentrated which then solidified to give an off white solid.

後処理

  1. customthe reaction
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washrinsed with warm toluene (˜70° C., 500 mL)
  4. concentrationThe colorless filtrate was concentrated which
  5. customto give an off white solid

出典と根拠

ORDレコード
ord-fd5ab569a8474c3ea7670319fc4ea1db
出典データセット
uspto-grants-2016_03
特許番号
US09290476B2

反応ノート

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