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

HRID 978290Notes

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

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

filtrationThe solid was filtered
customdried
dissolutiondissolved in dichloromethane (300 ml)
additionThe solution was added
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-d01ac49d53114464a6fc26efeb2ed27e
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04663453

Reaction notes

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