Ethyl bromoacetate → Ethyl 1,3-dihydro-2H-isoindole-2-acetate

HRID 1064195Notes

Reaction equation

HRID 1064195 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][NH:2]1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[Cs+].[Cs+].CCCCCC>CN(C)C=O>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][N:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)[CH3:16]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8058HexaneHCID 10796Cesium carbonateHCID 422478Isoindoline

Product 1

HCID 954470Ethyl 1,3-dihydro-2H-isoindole-2-acetateYield 37.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a solution of isoindoline (1.788 g, 15 mmol) and ethyl bromoacetate (2.756 g, 16.5 mmol) in N,N-dimethylformamide (20 mL), was added Cs2CO3 (5.376 g, 16.5 mmol) under N2. The mixture was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure and the resulting mixture was subjected to silica gel chromatography, eluting with 33:66 ethyl acetate:hexane to afford Intermediate 200(a) (1.14 g, 5.56 mmol) as a yellow oil in 37% yield.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washeluting with 33:66 ethyl acetate

Sources & evidence

ORD record
ord-13b99eba241d47ac9ff4b52a3a0529a0
Source dataset
uspto-grants-2005_11
Patent number
US06967198B2

Reaction notes

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