Phosphorus oxychloride → 8-Bromo-4-chloro-2-methylquinoline

HRID 1700113

반응식

HRID 1700113 반응식
[CH3:1][C:2]1[CH:11]=[C:10](O)[C:9]2[C:4](=[C:5]([Br:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.P(Cl)(Cl)([Cl:16])=O>>[CH3:1][C:2]1[CH:11]=[C:10]([Cl:16])[C:9]2[C:4](=[C:5]([Br:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychloride2회HCID 178428808HCID 178428808, 화합물

생성물 1

HCID 7684838-Bromo-4-chloro-2-methylquinoline수율 97%

반응 조건

온도
100 °C

실험 절차

Part A: To a quantity of 4.76 g (20 mmol) of 2-methyl-4-hydroxy-8-bromo-quinoline (J.Org.Chem. 1964, pg 3548) 15 ml of phosphorous oxychloride was added under ice-cooling. After heating to 100° C. for 30 minutes and subsequent cooling residual phosphorous oxychloride was removed by evaporation. After addition of ice water to the residue the mixture was neutralized with ammonia and extracted with CH2Cl2. The organic layer was dried over magnesium sulphate and concentrated in vacuo. The resulting product was purified on a silicagel column using ethylacetate as eluent. A total of 5.0 g of 2-methyl-4-chloro-8-bromo-quinoline was obtained (97% yield)

후처리

  1. temperaturecooling
  2. customwas removed by evaporation
  3. additionAfter addition of ice water to the residue the mixture
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe resulting product was purified on a silicagel column

출처 및 근거

ORD 기록
ord-70289fe802a84213abf80a354fa905cc
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350750B1

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