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

HRID 1730388Notes

Reaction equation

HRID 1730388 reaction equation
C1O[C:4]([CH2:6][N:7]2[C:11](=[O:12])[C:10]3=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]3[C:8]2=[O:17])([CH3:5])[O:3]C1.[Br:19]Br>C(O)COCCO>[C:11]1(=[O:12])[N:7]([CH2:6][C:4](=[O:3])[CH2:5][Br:19])[C:8](=[O:17])[C:9]2=[CH:16][CH:15]=[CH:14][CH:13]=[C:10]12

Participants

4

Reactant 2

HCID 24408BromineHCID 127071162-[(2-Methyl-1,3-dioxolan-2-yl)methyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 2220372-(3-bromo-2-oxopropyl)-2,3-dihydro-1H-isoindole-1,3-dioneYield 70.9%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A solution of phthalimidoacetone ethylene ketal (2.47 g, 10 mmole) in 10 mlof diethylene glycol is heated on a steambath. To this hot solution bromine(1.6 g, 10 mmole) is added dropwise under nitrogen. The reaction mixture iscooled to room temperature and is quenched in 20 ml hexane. To this mixtureis added solid sodium carbonate followed by chloroform and ice water. The organic layer is separated and the aqueous layer is extracted 3 times withchloroform. The chloroform extracts are washed with water, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue is crystallized from ethyl acetate/hexane to afford 2 g (55%) of (3-phthalimidoacetonyl)bromide, ethylene ketal as white prisms of melting point 139°-141° C. An analytical sample has a melting point of 140°-141° C.

Workup

  1. customiscooled to room temperature
  2. customis quenched in 20 ml hexane
  3. additionTo this mixtureis added solid sodium carbonate
  4. customThe organic layer is separated
  5. extractionthe aqueous layer is extracted 3 times withchloroform
  6. washThe chloroform extracts are washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated in vacuo
  9. customThe residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e86698a3bae247f08e7b36a409820ba3
Source dataset
uspto-grants-1976_11
Patent number
US03992408

Reaction notes

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