1,2-Dibromoethane → 1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-

HRID 612362Notes

Reaction equation

HRID 612362 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[Br:13][CH2:14][CH2:15]Br>CN(C=O)C>[Br:13][CH2:14][CH2:15][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

4

Reactant 2

HCID 78391,2-DibromoethaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-Yield 76.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium phthalimide (30.8 g, 0.17 M) is stirred at room temperature for 48 hours with 1,2-dibromoethane (63.9 g, 0.34 M) and dry DMF (374 ml). (DMF is dimethyl formamide.) The precipitated KBr is filtered off, and the liquids are removed from the filtrate by distillation. The brown solid residue is recrystallized from cyclohexane-heptane (10:1) to give nearly colorless crystals (32.3 g, 72.3%, m.p. 73-75° C.).

Workup

  1. filtration(DMF is dimethyl formamide.) The precipitated KBr is filtered off
  2. customthe liquids are removed from the filtrate by distillation
  3. customThe brown solid residue is recrystallized from cyclohexane-heptane (10:1)

Sources & evidence

ORD record
ord-18d11b949cf84a2398a76a66e3049287
Source dataset
uspto-grants-1999_12
Patent number
US06004826

Reaction notes

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