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

HRID 1507305ノート

反応式

HRID 1507305 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 10: 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 provide the title compound as 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

出典と根拠

ORDレコード
ord-04d63648544e44e3b12b6c25f7ab2acd
出典データセット
uspto-grants-2015_12
特許番号
US09221804B2

反応ノート

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