1,3-Dibromobutane → 130400-64-5

HRID 2248303Notes

Reaction equation

HRID 2248303 reaction equation
Br[CH2:2][CH2:3][CH:4]([Br:6])[CH3:5].[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12.[K]>CN(C)C=O>[Br:6][CH:4]([CH3:5])[CH2:3][CH2:2][N:11]1[C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]2[C:7]1=[O:17]

Participants

4

Reactant 2

HCID 78891,3-DibromobutaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 4548516130400-64-5

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

1,3 dibromobutane (10.8 g, 0.05 mol) and potassium phthalimide (9.25 g, 0.05 mol) were added to dry N,N dimethylformamide (100 ml) and the resulting mixture stirred at ambient temperature (20° C.) overnight. The resulting mixture was filtered to remove any solid and the solvent removed from the filtrate to give a colourless oil. The product, N-(3-bromobutyl)phthalimide, was isolated from the oil by flash chromatography on a silica gel column using silica gel, 230 to 400 US mesh (0.062 mm to 0.037 mm) eluted with 2% methanol in dichloromethane as a brown solid in a yield of 7.9 g (55.7%).

Workup

  1. filtrationThe resulting mixture was filtered
  2. customto remove any solid
  3. customthe solvent removed from the filtrate
  4. customto give a colourless oil

Sources & evidence

ORD record
ord-594be35490f14b1b895ffab5e90e5a6c
Source dataset
uspto-grants-1991_08
Patent number
US05039686

Reaction notes

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