Phosphine tribromide → 2-[5-(Bromomethyl)thiophen-2-yl]benzonitrile

HRID 2048606ノート

反応式

HRID 2048606 の反応式
O[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])=[CH:5][CH:4]=1.[Br-:16].[Br-].[Br-].P>C1(C)C=CC=CC=1>[Br:16][CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])=[CH:5][CH:4]=1

参加物

4

反応物 2

HCID 21862892Phosphine tribromideHCID 670088992-[5-(Hydroxymethyl)thiophen-2-yl]benzonitrile

生成物 1

HCID 670086562-[5-(Bromomethyl)thiophen-2-yl]benzonitrile収率 121.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution (50 mL) of 2-[5-(hydroxymethyl)thiophen-2-yl]benzonitrile (2.60 g) in toluene was added phosphine tribromide (2.60 g) at room temperature, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The obtained ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (3.20 g, 95%).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe obtained ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-5108964e75254b1094b19d8a7fc96c36
出典データセット
uspto-grants-2013_11
特許番号
US08592431B2

反応ノート

読み込み中…