Hydrogen Bromide → 1-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone

HRID 545074ノート

反応式

HRID 545074 の反応式
N[C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.N([O-])=O.[Na+].[BrH:19].[OH-].[Na+]>S(=O)(=O)(O)O.O>[Br:19][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1

参加物

7

反応物 4

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 586455412-Acetyl-5-amino-3-trifluoromethylpyridine

生成物 1

HCID 586455621-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 1-(5-amino-3-trifluoromethyl-pyridin-2-yl)-ethanone (408 mg, 2.0 mmol) in 75% sulfuric-acid (6 mL) at 0° C. add sodium nitrite (152 mg, 2.2 mmol) in water (1 mL). Stir the mixture for 30 minutes and add CuBr (343 mg, 2.4 mmol) and 48% HBr (2 mL). Heat the mixture at 60° C. for 30 minutes, cool to 0° C. and basify by dropwise addition of 10M sodium hydroxide. Extract the mixture with ethyl acetate (3×20 mL) and wash the combined organics with brine (50 mL). The organic extract is dried over MgSO4 and the solvent removed under reduced pressure to yield the title compound.

後処理

  1. temperaturecool to 0° C.
  2. extractionExtract the mixture with ethyl acetate (3×20 mL)
  3. washwash the combined organics with brine (50 mL)
  4. extractionThe organic extract
  5. dry with materialis dried over MgSO4
  6. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-bbfb7c8913f64d06941b8834c6ce0f39
出典データセット
uspto-grants-2011_05
特許番号
US07935702B2

反応ノート

読み込み中…