N-Hydroxyphthalimide → HCID 14049968, compound

Participants

Reaction Steps

N-hydroxyphthalimide (2.19, 0.018 mole) was dissolved in a mixture of dry dimethoxyethane (15 ml) and dry dimethyl sulphoxide (4 ml). The clear yellow solution was cooled to 25° and potassium carbonate (1.24 g, 0.009 mol) was added. A red suspension resulted. 4-Fluoro-3-phenoxybenzyl bromide (5 g, 0.018 mol) was added dropwise over 5h at 22°-28°. The reaction mixture was stirred at room temperature overnight, after which most of the dimethoxyethane was removed in vacuo, and the solution then quenched by pouring into dilute hydrochloric acid (100 ml 1%). The resulting slurry was filtered, and the crystals washed with distilled water and dried in vacuo to give N-(4-fluoro-3-phenoxybenzyloxy)phthalimide as white crystals (6.4 g), (98%), m.p. 88.2°.

Provenance & Evidence