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

HRID 4093Notes

Reaction equation

HRID 4093 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 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.

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-e608e546edba4941a2b95b36e8acb710
Source dataset
uspto-grants-1988_02
Patent number
US04723003

Reaction notes

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