Ethyl 3-bromopropionate → Ethyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoate

HRID 346241Notes

Reaction equation

HRID 346241 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][CH2:6]Br)[CH3:2].[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:8])[CH2:5][CH2:6][N:13]1[C:9](=[O:19])[C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]1=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 68320Ethyl 3-bromopropionateHCID 24194345Phthalimide potassium salt

Product 1

HCID 2797145Ethyl 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanoateYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure used to prepare 1,3-dihydro-1,3-dioxo-2H-isoindoleoctanoic acid ethyl ester. Thus, a mixture of 100.0 g (0.55 mole) of 3-bromopropionic acid ethyl ester (99%, Aldrich) and 108.7 g (0.58 mole) of potassium phthalimide (98%, Aldrich) in 300 mL of dimethylformamide gave 59.4 g (44%) of crude title compound as an oily residue. A 3.0 g sample of this oil was purified by high-pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrepPak® 500 silica; ethyl acetate-hexanes, 1:10). Fractions containing title compound were combined and the solvents evaporated under reduced pressure to give 2.3 g (77% recovery) of a pale-yellow oil.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-d83b91f2cf1f42dbbedca8a714afe1aa
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Reaction notes

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