Phenol → 2-Methyl-4-phenoxy-8-bromo-quinoline

HRID 1700114노트

반응식

HRID 1700114 반응식
[CH3:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[C:5]([Br:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[K+]>C(Cl)Cl>[CH3:1][C:2]1[CH:11]=[C:10]([O:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]2[C:4](=[C:5]([Br:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

참가 물질

5

반응물 3

HCID 996PhenolHCID 14797Potassium HydroxideHCID 7684838-Bromo-4-chloro-2-methylquinoline

생성물 1

HCID 183178152-Methyl-4-phenoxy-8-bromo-quinoline수율 84.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
120 °C

실험 절차

Part B: A mixture of 5.0 g (19.5 mmol) of 2-methyl-4-chloro-8-bromo-quinoline, 18.3 g (195 mmol) of phenol and 2.5 g (87%, 39 mmol) of KOH was heated at 120° C. under nitrogen for 30 min. After cooling 500 ml of CH2Cl2 was added and the mixture was extracted with 250 ml of 1N NaOH. After concentration of the organic layer in vacuo the residue was dissolved in ether and again extracted with 50 ml of 1N NaOH and 50 ml of brine. The organic layer was dried over magnesium sulphate and concentrated in vacuo. A total of 5.2 g of 2-methyl-4-phenoxy-8-bromo-quinoline was obtained as a white solid (85% yield).

후처리

  1. additionwas added
  2. extractionthe mixture was extracted with 250 ml of 1N NaOH
  3. dissolutionAfter concentration of the organic layer in vacuo the residue was dissolved in ether
  4. extractionagain extracted with 50 ml of 1N NaOH and 50 ml of brine
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-42e6c802722443f5884c5a1eaf0fd463
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350750B1

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