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

HRID 1942631노트

반응식

HRID 1942631 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 24593copper(I) bromide촉매HCID 24611Copper bromide (CuBr2)촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8b86e56db2c84ed3a0c9ac1afcf6695d
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

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