Water → HCID 18629321, compound

HRID 377284Notes

Reaction equation

HRID 377284 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:16]=[C:17]([CH2:24]Br)[C:18]([CH2:22]Br)=[C:19]([F:21])[CH:20]=1.O>CN(C)C=O>[Br:14][C:15]1[CH:16]=[C:17]2[C:18](=[C:19]([F:21])[CH:20]=1)[CH2:22][N:13]([S:10]([C:7]1[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=1)(=[O:12])=[O:11])[CH2:24]2

Participants

6

Reactant 4

HCID 962WaterHCID 6269P-ToluenesulfonamideHCID 24758Sodium hydrideHCID 18629356HCID 18629356, compound

Product 1

HCID 18629321HCID 18629321, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

In 30 ml of N,N-dimethylformamide was suspended 1.30 g of sodium hydride (purity: 60%), and 15 ml of a N,N-dimethylformamide solution containing 2.80 g of p-toluenesulfonamide was added thereto at room temperature, after which the resulting mixture was stirred at the same temperature for 30 minutes and then at 60° C. for 1 hour. A solution of 5.70 g of 5-bromo-2,3-di(bromomethyl)fluorobenzene in 15 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 10 minutes. The reaction mixture was added to 200 ml of water and the precipitate was collected by filtration to obtain 2.40 g of 5-bromo-7-fluoro-2-(p-toluenesulfonyl)isoindoline as colorless crystals.

Workup

  1. additionwas added
  2. waitat 60° C. for 1 hour
  3. stirringthe resulting mixture was stirred at the same temperature for 10 minutes
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c60261da44a14749b39937e8b08cc036
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

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