1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → 2-(2-Diethoxyphosphorylethyl)isoindole-1,3-dione

HRID 870127Notes

Reaction equation

HRID 870127 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14].[P:15]([O:22]CC)([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]>>[O:14]=[C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12](=[O:13])[N:4]1[CH2:3][CH2:2][P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]

Participants

3

Reactant 2

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 31215Triethyl phosphite

Product 1

HCID 2543772-(2-Diethoxyphosphorylethyl)isoindole-1,3-dione

Conditions

Temperature
130 °C

Procedure

Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 2-(2-bromoethyl)isoindoline-1,3-dione (8 g, 31.50 mmol, 1.00 equiv) and triethyl phosphite (6.2 g, 37.35 mmol, 1.19 equiv). The resulting solution was stirred for 18 h at 130° C. The resulting mixture was concentrated under vacuum. The crude product was re-crystallized from ether:n-hexane (1:2). This resulted in 5 g (48%) of diethyl 2-(1,3-dioxoisoindolin-2-yl)ethylphosphonate as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThe crude product was re-crystallized from ether:n-hexane (1:2)
  5. customThis resulted in 5 g (48%) of diethyl 2-(1,3-dioxoisoindolin-2-yl)ethylphosphonate as a white solid

Sources & evidence

ORD record
ord-6e2c4218755847219d5a1ce52305ea96
Source dataset
uspto-grants-2015_03
Patent number
US08969377B2

Reaction notes

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