1,4-Dibromobutane → N-(4-Bromobutyl)phthalimide

HRID 2108000Notes

Reaction equation

HRID 2108000 reaction equation
[K].[C:2]1(=[O:12])[NH:6][C:5](=[O:7])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]12.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]Br>CN(C)C=O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][N:6]1[C:2](=[O:12])[C:3]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:4]2[C:5]1=[O:7]

Participants

4

Reactant 2

HCID 80561,4-DibromobutaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 93575N-(4-Bromobutyl)phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of phthalimide potassium salt (2 g; 10.8 mmol), 1,4-dibromobutane (10.8 g; 50 mmol) and dry dimethylformamide (10 ml) was stirred at a bath temperature of 90 to 100° C. for 10 hours. The precipitated crystals were removed by filtration, and the filtrate was concentrated under reduced pressure. Excess of 1,4-dibromobutane was removed by distillation, and the residue was purified by silica gel column chromatography to give the objective compound. M.P., 81 -82° C.

Workup

  1. customThe precipitated crystals were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customExcess of 1,4-dibromobutane was removed by distillation
  4. customthe residue was purified by silica gel column chromatography
  5. customto give the objective compound
  6. customM.P., 81 -82° C.

Sources & evidence

ORD record
ord-4b7ca52353824ff3ad93688484c6e7cd
Source dataset
uspto-grants-1990_06
Patent number
US04937249

Reaction notes

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