Fenbufen → Phthalidyl 4-(4-biphenylyl)-4-oxobutyrate

HRID 371114

Reaction equation

HRID 371114 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C:7](=[O:13])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:30](=[O:31])[O:29]1>C(Cl)(Cl)Cl>[C:1]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:2]=[CH:3][C:4]([C:7](=[O:13])[CH2:8][CH2:9][C:10]([O:12][CH:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:30](=[O:31])[O:29]2)=[O:11])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 3335FenbufenHCID 8471TriethylamineHCID 962181(3H)-Isobenzofuranone, 3-bromo-

Product 1

HCID 12769707Phthalidyl 4-(4-biphenylyl)-4-oxobutyrateYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 7.5 g of 4-(4-biphenylyl)-4-oxobutyric acid in 40 ml of chloroform and 3.4 g of triethylamine is added a solution of 6.2 g of 3-bromophthalide in 20 ml of chloroform. The solution thus obtained is stirred 24 hours at room temperature, 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 to give the phthalidyl 4-(4-biphenylyl)-4-oxobutyrate; yield 73%.

Workup

  1. customThe solution thus obtained
  2. washthe organic phase is washed with an aqueous solution of sodium bicarbonate
  3. dry with materialwith water and finally it is dried on anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-acd74628f258460587cc31e2e8b25646
Source dataset
uspto-grants-1985_07
Patent number
US04529737

Linked notes

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