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

HRID 926458ノート

反応式

HRID 926458 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 12: 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 and the resulting residue 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

出典と根拠

ORDレコード
ord-77555f90f47d46629c970f24381e9f8c
出典データセット
uspto-grants-2016_03
特許番号
US09284308B2

反応ノート

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