Cesium carbonate → 4-Bromo-6-(2-methoxyethoxy)-2,3-dihydro-1H-isoindol-1-one

HRID 1247452Notes

Reaction equation

HRID 1247452 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:19][O:20][CH2:21][CH2:22]Br>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH2:22][CH2:21][O:20][CH3:19])[CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:12]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 219075354-Bromo-6-hydroxy-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 219075274-Bromo-6-(2-methoxyethoxy)-2,3-dihydro-1H-isoindol-1-oneYield 101.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 104B (100 mg, 0.44 mmol), Cs2CO3 (163 mg, 0.5 mmol) and 2-bromoethyl methyl ether (0.045 mL, 0.46 mmol) in DMF (2.2 mL) was warmed to 60° C. for 4 hours, stirred at room temperature overnight, and partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4), filtered, and concentrated to give 128 mg of the desired product. MS (ESI(+)) m/e 286,288 (M+H)+.

Workup

  1. custompartitioned between water and ethyl acetate
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2f2dc0653cac491ca24c37c70174eea8
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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