Bromine → 2-(3-bromo-2-oxopropyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1366670Notes

Reaction equation

HRID 1366670 reaction equation
[C:1]1(=[O:15])[N:5]([CH2:6][C:7](=[O:9])[CH3:8])[C:4](=[O:10])[C:3]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:2]12.[Br:16]Br>C(O)COCCO>[Br:16][CH2:8][C:7](=[O:9])[CH2:6][N:5]1[C:4](=[O:10])[C:3]2[C:2](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:1]1=[O:15]

Participants

4

Reactant 2

HCID 24408BromineHCID 235046Phthalimidoacetone

Product 1

HCID 2220372-(3-bromo-2-oxopropyl)-2,3-dihydro-1H-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
0 °C

Procedure

Commercially available phthalimidoacetone (2.0 g, 9.8522 mmol), under a nitrogen atmosphere, was taken up in diethylene glycol (13 mL) and cooled to 0° C. in an ice bath. Bromine (0.51 mL, 9.9242 mmol) was added dropwise. The reaction was shielded from light, allowed to reach ambient temperature, and stirred overnight. LCMS: (M+H)+=282.0.

Workup

  1. customto reach ambient temperature

Sources & evidence

ORD record
ord-dbc80023b77b400793e4654e26238476
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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