Tert-Butyl nitrite → 2-Bromo-3-chloro-6-fluoropyridine

HRID 1521942ノート

反応式

HRID 1521942 の反応式
[Br:1][C:2]1[N:7]=[C:6](N)[CH:5]=[CH:4][C:3]=1[Cl:9].C(ON=O)(C)(C)C.[FH:17].N1C=CC=CC=1>ClCCl>[Br:1][C:2]1[C:3]([Cl:9])=[CH:4][CH:5]=[C:6]([F:17])[N:7]=1

参加物

5

反応物 3

HCID 10906Tert-Butyl nitriteHCID 64774Pyridine, hydrofluoride (1:1)HCID 534011936-Bromo-5-chloropyridin-2-amine

生成物 1

HCID 754123402-Bromo-3-chloro-6-fluoropyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 6-bromo-5-chloropyridin-2-amine (1 g, 4.82 mmol) in dichloromethane (10 mL) at 0° C. added tert-butylnitrite (1.145 mL, 9.64 mmol) followed by pyridine hydrofluoride (3 mL, 9.64 mmol) and the mixture was stirred at 0° C. for 30 minutes. The mixture was quenched with water and extracted with dichloromethane. The organic layer was washed with water and brine (25 mL each), dried over sodium sulfate, filtered, and concentrated to afford of the title compound. 1H NMR (400 MHz, CDCl3): δ 6.90-6.93 (m, 1H), 7.80-7.84 (m, 1H).

後処理

  1. customThe mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water and brine (25 mL each)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-89a2ff2821fd454fa7082145654a9c3f
出典データセット
uspto-grants-2015_07
特許番号
US09073922B2

反応ノート

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