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

HRID 34382Notes

Reaction equation

HRID 34382 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)([O-:3])=[O:2].[Br:20]N1C(=O)CCC1=O.O>CN(C)C=O>[N+:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[N:11]1[C:19]2[C:14](=[CH:15][C:16]([Br:20])=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 138233471-(2-Nitro-4-bromophenyl)indoline

Product 1

HCID 138233441-(2-Nitro-4-bromophenyl)-5-bromoindolineYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

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 1) with vigorous stirring. The solid was filtered, dried, and dissolved in dichloromethane (300 ml). The solution was added to boiling methanol (1 1). The precipitate was collected by filtration to give 12.7 g (68%) of product, mp 150°-152° C.

Workup

  1. filtrationThe solid was filtered
  2. customdried
  3. dissolutiondissolved in dichloromethane (300 ml)
  4. additionThe solution was added
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-579195b9a184404b93734ef3ac850a84
Source dataset
uspto-grants-1988_08
Patent number
US04761412

Reaction notes

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