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

HRID 734815ノート

反応式

HRID 734815 の反応式
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

参加物

5

反応物 3

HCID 260Hydrogen Bromide2 回HCID 23668193Sodium NitriteHCID 859697042-Bromo-5-(4-chloro-phenyl)-pyridin-3-ylamine

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8d394aa56b1a4864ac852ddd2f068389
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

反応ノート

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