Ethyl bromoacetate → 1-Ethoxycarbonyl-5-chloro-3-phenylisoindole-2-acetic acid ethyl ester

HRID 1973299Notes

Reaction equation

HRID 1973299 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]=1[CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[O:5])[CH3:2].[CH2:22]([O:24][C:25](=[O:28])[CH2:26]Br)[CH3:23]>CS(C)=O>[CH2:22]([O:24][C:25](=[O:28])[CH2:26][N:7]1[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:9]2[C:14]([CH:13]=[CH:12][C:11]([Cl:15])=[CH:10]2)=[C:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH3:23]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 54174784Ethyl 5-chloro-3-phenyl-2H-isoindole-1-carboxylate

Product 1

HCID 545612521-Ethoxycarbonyl-5-chloro-3-phenylisoindole-2-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 30.0 g. of 5-chloro-3-phenylisoindole-1-carboxylic acid ethyl ester in 300 ml. of dimethylsulfoxide is treated with 66.8 g. of bromoacetic acid ethyl ester and 27.6 g. of finely triturated, dry potassium carbonate and intensively stirred at room temperature for 17 hours. The mixture is poured into 750 ml. of ice-water and the separated product, after the addition of 50 g. of sodium chloride, is removed by filtration under suction, washed with water and then dissolved in methylene chloride. The aqueous layer is separated, the organic phase dried over sodium sulfate, filtered and concentrated to dryness. The resulting oil crystallizes on trituration with ether and pentane, and there is obtained 1-ethoxycarbonyl-5-chloro-3-phenylisoindole-2-acetic acid ethyl ester; melting point 100°-101° C. Recrystallization from ethanol increases the melting point to 103°-104° C.

Workup

  1. customof finely triturated
  2. additionThe mixture is poured into 750 ml
  3. additionof ice-water and the separated product, after the addition of 50 g
  4. customof sodium chloride, is removed by filtration under suction
  5. washwashed with water
  6. dissolutiondissolved in methylene chloride
  7. customThe aqueous layer is separated
  8. dry with materialthe organic phase dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customThe resulting oil crystallizes on trituration with ether and pentane

Sources & evidence

ORD record
ord-2e2e05f0ebd44507a23749bab620dd83
Source dataset
uspto-grants-1976_12
Patent number
US03996374

Reaction notes

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