1(3H)-Isobenzofuranone, 3-bromo- → Phthalidyl 2-(4-isobutylphenyl)propionate

HRID 371109

Reaction equation

HRID 371109 reaction equation
Br[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[O:3]1.[CH2:12]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:26])[C:23]([O-:25])=[O:24])=[CH:18][CH:17]=1)[CH:13]([CH3:15])[CH3:14].[Na+]>CN(C)C=O>[CH2:12]([C:16]1[CH:17]=[CH:18][C:19]([CH:22]([CH3:26])[C:23]([O:25][CH:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4](=[O:5])[O:3]2)=[O:24])=[CH:20][CH:21]=1)[CH:13]([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 5338317Ibuprofen, Sodium Salt

Product 1

HCID 12769702Phthalidyl 2-(4-isobutylphenyl)propionateYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10.65 g of 3-bromophthalide in 100 ml of dimethylformamide, 11.5 g of sodium 2-(4-isobutylphenyl)propionate is added under stirring at room temperature. The reaction mixture is stirred 24 hours at room temperature, and it is then poured into 500 ml of ice water. After extraction with chloroform, the organic phase is washed with an aqueous solution of sodium bicarbonate, then with water and finally it is dried on anhydrous sodium sulfate and evaporated to dryness. The residue, crystallized from petroleum ether, yields 12.3 g of phthalidyl 2-(4-isobutylphenyl)propionate, having the same physico-chemical characteristics of the compounds of Example 1.

Workup

  1. stirringThe reaction mixture is stirred 24 hours at room temperature
  2. extractionAfter extraction with chloroform
  3. washthe organic phase is washed with an aqueous solution of sodium bicarbonate
  4. dry with materialwith water and finally it is dried on anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customThe residue, crystallized from petroleum ether

Sources & evidence

ORD record
ord-98155d8092aa46d49bd0d7003efbfb66
Source dataset
uspto-grants-1985_07
Patent number
US04529737

Linked notes

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