Triethylamine → Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetate

HRID 2361934Notes

Reaction equation

HRID 2361934 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[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>ClCCl.C(Cl)(Cl)Cl>[O:7]=[C:6]1[C:5]2[C:4](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3](=[O:12])[N:2]1[O:1][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 12919120Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)acetateYield 96.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-hydroxyphthalimide (16.31 g, 100 mmol) in dichloromethane (300 ml) was added triethylamine (20.91 ml, 150 mmol) and the mixture was stirred at 0° C. tert-Butyl bromoacetate (14.77 ml, 100 mmol) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with chloroform (100 ml) and washed with water (300 ml). The organic layer was washed with brine (300 ml) and dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo. n-Hexane:ethyl acetate (80:20, 100 ml) was added to the residue and the obtained precipitate was collected by filtration to obtain the title compound (26.72 g, 96%).

Workup

  1. additionwas added
  2. washwashed with water (300 ml)
  3. washThe organic layer was washed with brine (300 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. additionn-Hexane:ethyl acetate (80:20, 100 ml) was added to the residue
  8. filtrationthe obtained precipitate was collected by filtration

Sources & evidence

ORD record
ord-fe9d03e3aebf488f9c2a7c17f2b3b05b
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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