P-Toluenesulfonamide → 5-Bromo-2-(p-tolylsulfonyl)isoindoline

HRID 377279Notes

Reaction equation

HRID 377279 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:8][CH:9]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[C:17]([CH2:23]Br)[CH:16]=1>CN(C)C=O>[Br:14][C:15]1[CH:16]=[C:17]2[C:18](=[CH:19][CH:20]=1)[CH2:21][N:13]([S:10]([C:7]1[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=1)(=[O:12])=[O:11])[CH2:23]2

Participants

5

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 24758Sodium hydrideHCID 124964654-Bromo-1,2-bis(bromomethyl)benzene

Product 1

HCID 151678985-Bromo-2-(p-tolylsulfonyl)isoindolineYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
60 °C

Procedure

In 70 ml of N,N-dimethylformamide was suspended 3.97 g of sodium hydride (purity: 60%), followed by adding thereto 50 ml of a N,N-dimethylformamide solution containing 8.49 g of p-toluenesulfonamide, and the resulting mixture was stirred at 60° C. for 30 minutes. A solution of 17.0 g of 1-bromo-3,4-di(bromomethyl)benzene in 50 ml of N,N-dimethylformamide was added to the reaction mixture at 60° C. and the resulting mixture was stirred at the same temperature for 1 hour. The reaction mixture obtained was added to 500 ml of ice water and the precipitate was collected by filtration and purified by a column chromatography (eluent: chloroform) to obtain 15.2 g of 5-bromo-2-(p-toluenesulfonyl)isoindoline as colorless crystals.

Workup

  1. additionby adding
  2. stirringthe resulting mixture was stirred at the same temperature for 1 hour
  3. customThe reaction mixture obtained
  4. filtrationthe precipitate was collected by filtration
  5. custompurified by a column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-6762d1b3c3134b589a54c7ff8dd6592a
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

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