Sulfuric Acid → 2-(4-Bromo-3-oxobutyl)-1H-isoindole-1,3(2H)-dione

HRID 915679

Reaction equation

HRID 915679 reaction equation
[O:1]=[C:2]([CH3:16])[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[Br:17]Br.S(=O)(=O)(O)O>CO>[Br:17][CH2:16][C:2](=[O:1])[CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24408BromineHCID 2907282-(3-Oxobutyl)isoindoline-1,3-dione

Product 1

HCID 37597442-(4-Bromo-3-oxobutyl)-1H-isoindole-1,3(2H)-dioneYield 24.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepare a cold (0° C.) solution of 2-(3-oxobutyl)isoindole-1,3-dione (6.8 g, 31.5 mmol) in methanol (50 mL). Add Br2 (3.2 mL, 63 mmol). Allow the reaction to warm to room temperature and stir for 15 hours. Add 10 M sulfuric acid (26 mL) and stir the mixture for 15 hours. Filter off the solids and dry in vacuo to afford 2-(4-bromo-3-oxobutyl)isoindole-1,3-dione (2.3 g).

Workup

  1. customthe reaction
  2. stirringstir the mixture for 15 hours
  3. filtrationFilter off the solids
  4. customdry in vacuo

Sources & evidence

ORD record
ord-736dea6486824a4bb56436fa6faa2d2e
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Linked notes

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