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

HRID 526835노트

반응식

HRID 526835 반응식
[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]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 5359268AluminumHCID 10942334Sodium MethoxideHCID 867156286-Bromo-2,4-dichloro-3-(4-(trifluoromethyl)benzyl)quinoline2회

생성물 1

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

시약·촉매·용매 1

HCID 21226440Methylenechloride Hexane용매

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온도
80 °C

실험 절차

To a 1 L flask containing 6-bromo-2,4-dichloro-3-(4-(trifluoromethyl)benzyl)quinoline (32.5 g, 74.7 mmol, Intermediate 5: 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 afford the title compound as an off white solid.

후처리

  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

출처 및 근거

ORD 기록
ord-d17bbea1afb0401bbb779c9c475c1fe3
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346782B2

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