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

HRID 1700113ノート

反応式

HRID 1700113 の反応式
[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

参加物

3

反応物 2

HCID 24813Phosphorus oxychloride2 回HCID 178428808HCID 178428808、化合物

生成物 1

HCID 7684838-Bromo-4-chloro-2-methylquinoline収率 97%

反応条件

温度
100 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-70289fe802a84213abf80a354fa905cc
出典データセット
uspto-grants-2002_02
特許番号
US06350750B1

反応ノート

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