Ammonia → 3,5-Dibromo-2-(trifluoromethyl)pyridine

HRID 1892224ノート

反応式

HRID 1892224 の反応式
I[C:2]1[C:7]([Br:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[F-].[K+].[F:12][C:13]([Si](C)(C)C)([F:15])[F:14].N>CN1C(=O)CCC1.[Cu]I>[Br:8][C:7]1[C:2]([C:13]([F:15])([F:14])[F:12])=[N:3][CH:4]=[C:5]([Br:9])[CH:6]=1

参加物

7

反応物 4

HCID 222AmmoniaHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 269675523,5-Dibromo-2-iodopyridine

生成物 1

HCID 110449423,5-Dibromo-2-(trifluoromethyl)pyridine収率 46.1%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
50 °C

実験手順

To a solution of 2-iodo-3,5-dibromopyridine (4.21 g, 11.60 mmol) in NMP (25 mL) were added copper(I) iodide (4.42 g, 23.21 mmol), potassium fluoride (1.35 g, 23.21 mmol), and (trifluoromethyl)trimethylsilane (5.61 mL, 35.90 mmol). The resulting mixture was allowed to stir overnight at 50° C. The mixture was poured into 12% aqueous ammonia, and then extracted with Et2O (2×120 mL). The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3,5-dibromo-2-(trifluoromethyl)pyridine (1.63 g, 46%) as a liquid.

後処理

  1. extractionextracted with Et2O (2×120 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-65350ca69df54dc88472cff7230cbbf0
出典データセット
uspto-grants-2013_08
特許番号
US08507667B2

反応ノート

読み込み中…