Phthalimide → Methyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)benzoate

HRID 1762169Notes

Reaction equation

HRID 1762169 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.[K].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12>CN(C)C=O>[CH3:12][O:11][C:9]([C:8]1[CH:13]=[CH:14][C:5]([O:4][CH2:3][CH2:2][N:20]2[C:19](=[O:21])[C:18]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]3[C:16]2=[O:26])=[CH:6][CH:7]=1)=[O:10]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 1898264Methyl 4-(2-bromoethoxy)benzoateHCID 5462222Potassium

Product 1

HCID 7679064Methyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)benzoateYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-(2-Bromoethoxy)benzoate (126.52 g) and 99.5 g of potassium salt of phthalimide were dissolved in 600 ml of N,N-dimethylformamide and the solution was stirred at 78°-80° C. for 2 hours. The reaction solution was poured over ice water and extracted with chloroform. The chloroform layer was washed with water twice, dried with anhydrous magnesium sulphate, and concentrated in vacuo whereupon the residue was crystallised. Ether was added to the residue and filtered to give crystals in 149.23 g (yield: 94%). M.p. 129°-130.5° C.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform layer was washed with water twice
  3. dry with materialdried with anhydrous magnesium sulphate
  4. concentrationconcentrated in vacuo whereupon the residue
  5. customwas crystallised
  6. additionEther was added to the residue
  7. filtrationfiltered
  8. customto give crystals in 149.23 g (yield: 94%)

Sources & evidence

ORD record
ord-89aa20710e4e4a8c8ff3c0d15ac04285
Source dataset
uspto-grants-1989_05
Patent number
US04831055

Reaction notes

Loading…