Water → 1-(4-Bromo-2-fluorobenzyl)-7-trifluoromethylindoline-2,3-dione

HRID 1719229Notes

Reaction equation

HRID 1719229 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:21])([F:20])[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15](=[O:18])[C:14]2=[O:19].[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[C:25]([F:31])[CH:24]=1.O>CN(C)C=O.ClC1C=CC=CC=1.O1CCCC1>[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:16]2[C:17]3[C:13](=[CH:12][CH:11]=[CH:10][C:9]=3[C:8]([F:7])([F:20])[F:21])[C:14](=[O:19])[C:15]2=[O:18])=[C:25]([F:31])[CH:24]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6045757-TrifluoromethylisatinHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 132512921-(4-Bromo-2-fluorobenzyl)-7-trifluoromethylindoline-2,3-dione

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 7964ChlorobenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous potassium carbonate (10.7 g.) and 7-trifluoromethyl indoline-2,3-dione (14.4 g.) were stirred in N,N-dimethylformamide (DMF) (100 ml.) for 30 minutes. A portion (78.9 ml.) of a 25% w/v solution of 4-bromo-2-fluorobenzyl bromide in chlorobenzene was then added and the mixture was stirred at 75°-78° C. for 2 hours. The mixture was then cooled to ambient temperature and poured into water (400 ml.). Petrol 60-80 (200 ml.) was added to the aqueous mixture and the whole was stirred for 30 minutes. The solid which formed was separated by filtration to give 1-(4-bromo-2-fluorobenzyl)-7-trifluoromethyl indoline-2,3-dione (17.8 g.), m.p. 141°-143° C.

Workup

  1. stirringthe whole was stirred for 30 minutes
  2. customThe solid which formed
  3. customwas separated by filtration

Sources & evidence

ORD record
ord-cd230b9a548f42d9853ad6b52df645d4
Source dataset
uspto-grants-1985_09
Patent number
US04539329

Reaction notes

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