Hydrogen Bromide → 2,3-Dibromo-5-(4-chlorophenyl)pyridine

HRID 734815노트

반응식

HRID 734815 반응식
N([O-])=O.[Na+].[Br:5][C:6]1[C:11](N)=[CH:10][C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:8][N:7]=1.[BrH:20]>O>[Br:5][C:6]1[C:11]([Br:20])=[CH:10][C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:8][N:7]=1

참가 물질

5

반응물 3

HCID 260Hydrogen Bromide2회HCID 23668193Sodium NitriteHCID 859697042-Bromo-5-(4-chloro-phenyl)-pyridin-3-ylamine

생성물 1

HCID 860770432,3-Dibromo-5-(4-chlorophenyl)pyridine

시약·촉매·용매 1

HCID 962Water용매3회

반응 조건

온도
0 °C

실험 절차

A solution of 0.33 g (4.85 mmol) of sodium nitrite in 1.9 mL of water was added at 0° C. with vigorous stirring to a suspension of 1.25 g (4.41 mmol) of 2-bromo-5-(4-chlorophenyl)pyridin-3-ylamine in 9.90 mL (88.16 mmol) of 48% aqueous HBr and 9.90 mL of water and stirred for a further 10 minutes at 0° C. Subsequently a solution of 0.95 g (6.61 mmol) of CuBr in 3.47 mL of 48% aqueous HBr was added and the mixture was stirred for I hour at 60° C. The reaction mixture was diluted with water and exhaustively extracted with EtOAc. The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and water, dried over magnesium sulfate, and evaporated down in vacuo. The residue was purified by column chromatography (silica gel, PE/DCM 1:1). Yield: 1.00 g (65% of theoretical); C11H6Br2ClN (M=347.433); calc.: molpeak (M+H)+:346/348/350/352 (2BrCl); found: molpeak (M+H)+: 346/348/350/352 (2BrCl).

후처리

  1. stirringthe mixture was stirred for I hour at 60° C
  2. extractionexhaustively extracted with EtOAc
  3. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down in vacuo
  6. customThe residue was purified by column chromatography (silica gel, PE/DCM 1:1)

출처 및 근거

ORD 기록
ord-8d394aa56b1a4864ac852ddd2f068389
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592358B2

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