Phosphorus oxybromide → 2-Bromo-6-methoxyquinoline

HRID 2045715ノート

反応式

HRID 2045715 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[CH:7]=[CH:6]2.P(Br)(Br)([Br:16])=O>>[Br:16][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

参加物

3

反応物 2

HCID 24613Phosphorus oxybromideHCID 2282682-Hydroxy-6-methoxyquinoline

生成物 1

HCID 114704222-Bromo-6-methoxyquinoline収率 49.3%

反応条件

温度
140 °C

実験手順

6-Methoxyquinolin-2(1H)-one (6.81 g, 38.9 mmol) was carefully added to POBr3 (18.9 g, 66.1 mmol) at 60° C., and the resulting solution was stirred at 140° C. for 2.5 h. The reaction mixture was cooled and poured onto crushed ice, and the solid was collected by filtration. Purification of this material on silica gel (gradient elution from 5 to 12% EtOAc in petroleum ether) afforded the title compound (4.57 g, 49.3%) as a solid. LCMS (ES+) m/z 238, 240 (M+H)+.

後処理

  1. temperatureThe reaction mixture was cooled
  2. additionpoured
  3. customonto crushed ice
  4. filtrationthe solid was collected by filtration
  5. customPurification of this material on silica gel (gradient elution from 5 to 12% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-9042e30c9dd44a0ea7cfddb3ec75d3e9
出典データセット
uspto-grants-2013_11
特許番号
US08591878B2

反応ノート

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