Reaction #502123

Reaction equation

N-hydroxyphthalimide

K2CO3

tert-butyl bromoacetate

→

title compound

Yield 71.0%

tert-Butyl 2-(1,3-dioxobenzo(c)azolin-2-yloxy)acetate

Yield 71.0%

Solvents

DMF

Conditions

Workup

1. 1
   Otherthe solvent was evaporated under high vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
3. 3
   Washwashed with brine
4. 4
   Dryingdried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   OtherThe residue after evaporation of the solvent
7. 7
   Otherwas recrystallized from a mixture of CH2Cl2/EtOAc/hexane

Procedure

A mixture of N-hydroxyphthalimide (10 g, 61.3 mmol), K2CO3 (16.9 g, 122 mmol) and tert-butyl bromoacetate (12 g, 9 mL, 61.3 mmol) in DMF (60 mL) was stirred at room temperature for 3 hours and the solvent was evaporated under high vacuum. The residue was dissolved in EtOAc, washed with brine, dried over Na2SO4 and filtered. The residue after evaporation of the solvent was recrystallized from a mixture of CH2Cl2/EtOAc/hexane to give the title compound (12 g, 71% yield) as a white solid. Mp 140-141° C. 1H NMR (300 MHz, CDCl3) δ 7.80-7.90 (m, 2H), 7.74-7.77 (m, 2H), 4.71 (s, 2H), 1.49 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 166.0, 163.0, 134.7, 128.9, 123.7, 83.0, 73.5, 28.1. Mass spectrum (API-TIS) m/z 278 (MH−), 295 (MNH4+). Anal. calcd. for C14H15NO5: C, 60.64; H, 5.45; N, 5.05. Found C, 60.47; H, 5.31; N, 4.96.

Source