2-(1,3-dioxoisoindol-2-yl)oxyacetonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-hydroxyphthalimide (5.20 g, 31.88 mmol) in DMF (20 ml) was added bromoacetonitrile (3.0 ml, 45.02 mmol) and Et3N (10.0 ml, 71.8 mmol) and the reaction stirred at room temperature for 2 d. The mixture was diluted with EtOAc (50 ml) and brine (40 ml) and the organic layer was washed with brine (4×20 ml) and 1 N NaOH (30 ml), dried (Na2SO4) and concentrated to afford (1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-acetonitrile (2.3 g, 36%) as a beige solid. 1H NMR (CDCl3) δ 4.96 (s, 2H), 7.80-7.84 (m, 2H), 7.89-7.92 (m, 2H). the organic layer was washed with brine (4×20 ml) and 1 N NaOH (30 ml) dried (Na2SO4) concentrated