Dimethylformamide → HCID 86602520, compound

HRID 30683Notes

Reaction equation

HRID 30683 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.[K].CN(C)C=O>O>[O:23]=[C:21]1[C:20]2[C:19](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18](=[O:28])[N:22]1[CH2:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14557545HCID 14557545, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 86602520HCID 86602520, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of diethyl [3-(bromomethyl)benzyl]phosphonate (10 g), potassium phthalimide (5.77 g) and N,N-dimethylformamide (100 ml) was stirred at room temperature for 14 hrs. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated Recrystallization of the residue from ethyl acetate-hexane gave diethyl {3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzyl}phosphonate (9.40 g, 78%) as colorless prism crystals. melting point: 100-101° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5aa7077bbae146b68120441f98d98436
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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