Phosphorus tribromide → N-(5-Bromopentyl)phthalimide

HRID 1383387Notes

Reaction equation

HRID 1383387 reaction equation
[C:1]1(=[O:17])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]O)[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]12.P(Br)(Br)[Br:19].C(=O)([O-])O.[Na+]>C(OCC)C>[Br:19][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]2[C:1]1=[O:17]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 5948445-Phthalimido-1-pentanol

Product 1

HCID 136770N-(5-Bromopentyl)phthalimideYield 45%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Then, 16.2 g of 5-phthalimido-1-pentanol was dissolved in 350 ml of diethyl ether, and 4.3 ml of phosphorus tribromide was added dropwise at 0° C. The reaction solution was stirred at room temperature for 9 hours and neutralized with saturated aqueous sodium hydrogen carbonate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo for removal of the solvent. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1) to give 9.2 g of 1-bromo-5-phthalimidopentane in a yield of 45%.

Workup

  1. washthe organic layer was washed with saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated in vacuo for removal of the solvent
  4. customThe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-5a2f72c6b8624bcba505e179d0355566
Source dataset
uspto-grants-2001_07
Patent number
US06255321B1

Reaction notes

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