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

HRID 1754839Notes

Reaction equation

HRID 1754839 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.OS(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)-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-cooled and well-stirred suspension of 2-(3-oxo-butyl)-isoindole-1,3-dione (30.0 g, 138 mmol, 1 eq.) in MeOH (180 mL), bromine (14.3 mL, 276 mmol, 2 eq.) was added in one portion. The resulting red heterogeneous mixture was stirred at 0° C. for 5 min., and further at r.t. for 3.5 hours. The orange homogeneous reaction mixture was then treated with 10M aq. H2SO4 soln. (26.2 mL). The resulting heterogeneous mixture was further stirred at r.t. for 2 hours. The resulting heterogeneous reaction mixture was filtered in order to isolate the target product as a white-off solid which was further dried under high vacuum. The product was used without further purification.

Workup

  1. additionwas added in one portion
  2. stirringThe resulting red heterogeneous mixture was stirred at 0° C. for 5 min.
  3. stirringThe resulting heterogeneous mixture was further stirred at r.t. for 2 hours
  4. filtrationThe resulting heterogeneous reaction mixture was filtered in order
  5. customto isolate the target product as a white-off solid which
  6. customwas further dried under high vacuum
  7. customThe product was used without further purification

Sources & evidence

ORD record
ord-53076f3de9b34fb2a9228d2adaa46320
Source dataset
uspto-grants-2015_10
Patent number
US09169270B2

Reaction notes

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