Potassium Fluoride → 5-Bromo-3-fluoro-2-methylquinoxaline

HRID 1055954ノート

反応式

HRID 1055954 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5](Cl)[C:6]([CH3:12])=[N:7]2.[F-:14].[K+]>CS(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([F:14])[C:6]([CH3:12])=[N:7]2

参加物

4

反応物 2

HCID 522689Potassium FluorideHCID 894288875-Bromo-3-chloro-2-methylquinoxaline

生成物 1

HCID 897819405-Bromo-3-fluoro-2-methylquinoxaline収率 105%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
90 °C

実験手順

A 1-L, three-necked round-bottomed flask equipped with a mechanical stirrer, a nitrogen gas inlet, and a temperature probe was charged 5-bromo-3-chloro-2-methylquinoxaline (21.5 g, 83 mmol), DMSO (215 mL) and KF (4.85 mL, 209 mmol), and the resulting mixture was heated at 90° C. for 2.5 h. The mixture was cooled to RT and ice/water (430 mL) was added. The precipitated solid was collected by vacuum filtration and then washed with water (100 mL) and dried in vacuo to afford 5-bromo-3-fluoro-2-methylquinoxaline (126f; 21 g) as a brown solid, which was used without further purification in the subsequent step: 1H NMR (400 MHz, CDCl3) δ ppm 8.03 (1H, d, J=2.2 Hz), 8.01 (1H, d, J=1.2 Hz), 7.59 (1H, t, J=7.9 Hz), 2.79 (3H, d, J=1.4 Hz). 19F NMR (377 MHz, CDCl3) δ ppm −70.61 (1F, br. s.). m/z (ESI, +ve) 240.9 (M+H)+.

後処理

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe precipitated solid was collected by vacuum filtration
  3. washwashed with water (100 mL)
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-92895f95a9e34be6a4c8aaba9d25089c
出典データセット
uspto-grants-2016_07
特許番号
US09394297B2

反応ノート

読み込み中…