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

HRID 1521942노트

반응식

HRID 1521942 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-89a2ff2821fd454fa7082145654a9c3f
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073922B2

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