Hydrogen Bromide → 5-Bromo-2-(2-methylpropyl)benzonitrile

HRID 1942631

反応式

HRID 1942631 の反応式
N[C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH:11]([CH3:13])[CH3:12])=[C:6]([CH:9]=1)[C:7]#[N:8].[BrH:14].N([O-])=O.[Na+].C(=O)(O)[O-].[Na+]>C(#N)C.O.[Cu](Br)Br.[Cu]Br>[Br:14][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH:11]([CH3:13])[CH3:12])=[C:6]([CH:9]=1)[C:7]#[N:8]

参加物

9

反応物 4

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 222279325-Amino-2-(2-methylpropyl)benzonitrileHCID 23668193Sodium Nitrite

生成物 1

HCID 513581655-Bromo-2-(2-methylpropyl)benzonitrile

試薬・触媒・溶媒 4

HCID 24593copper(I) bromide触媒HCID 24611Copper bromide (CuBr2)触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 5-amino-2-isobutylbenzonitrile (D57) (34 g) in acetonitrile (500 mL) was added HBr (24.37 mL) at 0° C. Then a solution of sodium nitrite (16.16 g) in water (50 mL) was added to the reaction mixture. After stirring for 30 min, copper(II) bromide (87 g) and copper(I) bromide (5.60 g) were added to the reaction mixture. The mixture was stirred at room temperature for 16 h. Saturated aqueous sodium bicarbonate solution was added to quench the reaction. The mixture was extracted with EA. The combined organic solution was dried over anhydrous sodium sulphate. After filtration and concentration, the residue was purified by column chromatography to give 5-bromo-2-(2-methylpropyl)benzonitrile (D58) (36 g) as a colorless oil. 6H (CDCl3, 400 MHz): 0.96 (6H, d), 1.98 (1H, m), 2.69 (2H, d), 7.18 (1H, d), 7.64 (1H, dd), 7.55 (1H, d).

後処理

  1. stirringThe mixture was stirred at room temperature for 16 h
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted with EA
  5. dry with materialThe combined organic solution was dried over anhydrous sodium sulphate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-8b86e56db2c84ed3a0c9ac1afcf6695d
出典データセット
uspto-grants-2013_03
特許番号
US08389508B2

関連ノート

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