Phosphorus oxychloride → 1-(6-Bromo-4-chloroquinolin-3-yl)-2-methylpropan-1-one

HRID 2271514ノート

反応式

HRID 2271514 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[C:5]2O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.P(Cl)(Cl)([Cl:31])=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[C:5]2[Cl:31]

参加物

4

反応物 3

HCID 24813Phosphorus oxychlorideHCID 86584982Sodium bicarbonate ethyl acetateHCID 178450272HCID 178450272、化合物

生成物 1

HCID 680919931-(6-Bromo-4-chloroquinolin-3-yl)-2-methylpropan-1-one収率 89%

反応条件

温度
85 °C

実験手順

1-(6-Bromo-4-hydroxyquinolin-3-yl)-2-methylpropan-1-one (16.0 g, 54.4 mmol) was added to phosphoryl chloride (160 mL) and the reaction was stirred at 85° C. for 1.5 h. The reaction mixture was cooled and slowly poured into a 2:1 solution of satd. aq. sodium bicarbonate/ethyl acetate at 0° C. The organic layer was separated and was washed with satd. aq. sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford the desired product (14.8 g, 89%) as a yellow solid: ESI MS m/z 312 [C13H11BrClNO+H]+.

後処理

  1. temperatureThe reaction mixture was cooled
  2. additionslowly poured into a 2:1 solution of satd
  3. customat 0° C
  4. customThe organic layer was separated
  5. washwas washed with satd
  6. dry with materialaq. sodium bicarbonate and brine, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-f569a67eaae148e2ab98e47ffeeb9d99
出典データセット
uspto-grants-2015_09
特許番号
US09120749B2

反応ノート

読み込み中…