1,2-Dibromoethane → 1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethoxy)-

HRID 733331Notes

Reaction equation

HRID 733331 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C(N(CC)CC)C.[Br:20][CH2:21][CH2:22]Br>CN(C=O)C>[Br:20][CH2:21][CH2:22][O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 8471TriethylamineHCID 10665N-Hydroxyphthalimide

Product 1

HCID 1998751H-Isoindole-1,3(2H)-dione, 2-(2-bromoethoxy)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-Bromoethoxy)phthalimide was synthesised by a modification of the procedure of Bauer and Suresh (Bauer et al 1963). N-Hydroxyphthalimide (80 g, 0.49 mol), triethylamine (150 mL, 1.08 mol), and 1,2-dibromoethane (175 mL, 2.30 mol) were combined in DMF (575 mL) and stirred at room temperature overnight. Solids were filtered and washed with DMF and the filtrate was diluted with water (4.0 L) and the resulting precipitate filtered, dissolved in EtOAc (500 mL), and washed with 1 N HCl (2×100 mL), water (1×100 mL), and dried over MgSO4. Volatiles were removed in vacuo, and the resulting solid recrystallised from 95% EtOH to give (9) as a white solid (87.1 g, 70%): mp. 94-96° C.; lit. mp. 94-96° C. 1H NMR (CDCl3): δ 7.82 (m, 4H), 4.49 (t, 2H, J=6.9 Hz), 3.65 (t, 2H, J=6.9 Hz).

Workup

  1. filtrationSolids were filtered
  2. washwashed with DMF
  3. additionthe filtrate was diluted with water (4.0 L)
  4. filtrationthe resulting precipitate filtered
  5. dissolutiondissolved in EtOAc (500 mL)
  6. washwashed with 1 N HCl (2×100 mL), water (1×100 mL)
  7. dry with materialdried over MgSO4
  8. customVolatiles were removed in vacuo
  9. customthe resulting solid recrystallised from 95% EtOH

Sources & evidence

ORD record
ord-7da53d86bf974c389e2c5205d70099ac
Source dataset
uspto-grants-2009_09
Patent number
US07589170B1

Reaction notes

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