Reaction #4131

Reaction equation

1-(2-nitro-4-bromophenyl)indoline

N-bromosuccinimide

water

→

product

Yield 68.0%

1-(2-Nitro-4-bromophenyl)-5-bromoindoline

Yield 68.0%

Solvents

dimethylformamide

dimethylformamide

Conditions

Workup

1. 1
   FiltrationThe solid was filtered
2. 2
   Otherdried
3. 3
   workup.DISSOLUTIONdissolved in dichloromethane (300 ml)
4. 4
   workup.ADDITIONThe solution was added
5. 5
   FiltrationThe precipitate was collected by filtration

Procedure

To a solution of 1-(2-nitro-4-bromophenyl)indoline (15 g, 0.047 moles) in dimethylformamide (150 ml) at -10° C. was added dropwise a solution of N-bromosuccinimide (9.4 g, 0.054 mole) in dimethylformamide (50 ml) over 10 minutes. The reaction mixture was stirred at 0° C. for 15 minutes. The solution was added slowly to water (1 l) with vigorous stirring. The solid was filtered, dried, and dissolved in dichloromethane (300 ml). The solution was added to boiling methanol (1 l). The precipitate was collected by filtration to give 12.7 g (68%) of product, mp 150°-152° C.

Source