Hydrochloric Acid → 1-[(4-Bromo-2-fluorophenyl)methyl]-7-chloro-1H-indole-2,3-dione

HRID 64955Notes

Reaction equation

HRID 64955 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[C:7]2=[O:12].C(=O)([O-])[O-].[K+].[K+].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[C:22]([F:28])[CH:21]=1.Cl>CN(C)C=O.ClC1C=CC=CC=1.O>[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[Cl:1])[C:7](=[O:12])[C:8]2=[O:11])=[C:22]([F:28])[CH:21]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 3441357-ChloroisatinHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 132480821-[(4-Bromo-2-fluorophenyl)methyl]-7-chloro-1H-indole-2,3-dioneYield 50.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 7964ChlorobenzeneSolvent

Procedure

A suspension of 7-chloroindoline-2,3-dione (15 g.) and potassium carbonate (15 g.) in N,N-dimethylformamide (100 ml.) was stirred and treated with a solution of 4-bromo-2-fluorobenzyl bromide (24.7 g.) in chlorobenzene (100 ml.). The mixture was stirred at 90° C. for five hours, cooled to ambient temperature, and diluted with a mixture of water (500 ml.) and petrol ether (b.p 60°-80° C.) (500 ml.) The aqueous phase was adjusted to pH3 with 10M hydrochloric acid. The mixture obtained was separated by filtration. The solid obtained was washed with further petrol ether, then with water, and recrystallised from ethanol to give 1-(4-bromo-2-fluorobenzyl)-7-chloro-indoline-2,3-dione (15.5 g.), m.p. 164°-166° C.

Workup

  1. stirringThe mixture was stirred at 90° C. for five hours
  2. customThe mixture obtained
  3. customwas separated by filtration
  4. customThe solid obtained
  5. washwas washed with further petrol ether
  6. customwith water, and recrystallised from ethanol

Sources & evidence

ORD record
ord-2600c3531f164ac6aff29a8a7d681b69
Source dataset
uspto-grants-1986_09
Patent number
US04611062

Reaction notes

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