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

HRID 371110

Reaction equation

HRID 371110 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].[K+]>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 23662458Ibuprofen potassium

Product 1

HCID 12769702Phthalidyl 2-(4-isobutylphenyl)propionateYield 69.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10.65 g of 3-bromophthalide in 100 ml of dimethylformamide is added 12.2 g of potassium 2-(4-isobutylphenyl)propionate under stirring at room temperature. The reaction mixture is stirred 24 hours at room temperature, and 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 dried on anhydrous sodium sulfate and evaporated to dryness. The residue, crystallized from petroleum ether, yields 11.8 g of phthalidyl 2-(4-isobutylphenyl)propionate having the same physico-chemical characteristics of the compound 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 dried on anhydrous sodium sulfate
  5. customevaporated to dryness
  6. customThe residue, crystallized from petroleum ether

Sources & evidence

ORD record
ord-3cf17c503e574211a2bf4f12050d8423
Source dataset
uspto-grants-1985_07
Patent number
US04529737

Linked notes

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