Water → 5-Bromopentylphthalimide

HRID 21788

Reaction equation

HRID 21788 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][CH2:16][CH2:17][CH2:18]Br.O>CN(C)C=O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:4]([NH:5][C:1](=[O:11])[C:2]=12)=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 81001,5-DibromopentaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 223521765-BromopentylphthalimideYield 281.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium phthalimide (5.4 mmoles) was added to a solution of 1,5-dibromopentane (3.72 g; 16.2 mmoles) in dimethylformamide (8 ml) and heated to 80° C. approx. under stirring. After 2 hours, water was added and the solution was repeatedly extracted with ether. The collected organic phases were washed with water, dried on Na2SO4 and evaporated under reduced pressure to give a solid (4.50 g), which was purified by chromatography on silica gel (Etp/Et2O 8:2) yielding 2.38 g of a white solid. Yield 68%.

Workup

  1. temperatureheated to 80° C. approx.
  2. extractionthe solution was repeatedly extracted with ether
  3. washThe collected organic phases were washed with water
  4. customdried on Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-48a90d782a0f4ad6823194186ca6696b
Source dataset
uspto-grants-1995_06
Patent number
US05424451

Linked notes

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