Reaktion #1005

Reaktionsgleichung

4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid

benzoyl peroxide

N-bromosuccinimide

→

2-bromo-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid

Ausbeute 29.1%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe precipitate collected
2. 2
   Waschenrinsed with water
3. 3
   Trocknendiethyl ether and dried
4. 4
   SonstigePurification on Silica gel (5% methyl alcohol in 1:1:1 dichloromethane/ethyl acetate/hexanes)

Vorschrift

To a solution of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (886 mg, 5 mmol) and catalytic benzoyl peroxide in N,N-dimethylformamide (5 mL) at 0° C. was added N-bromosuccinimide (1.869 g, 10.5 mmol)in four equal portions over 1 hour. The mixture was stirred an additional hour, then poured into ice water, the precipitate collected and rinsed with water then diethyl ether and dried. Purification on Silica gel (5% methyl alcohol in 1:1:1 dichloromethane/ethyl acetate/hexanes) gave 2-bromo-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (376 mg).

Quelle