2-[(2,3,4,5,6-Pentafluorophenyl)methoxy]phthalimide

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-(Pentafluorobenzyloxy)phthalimide 15.9 g, 46 mmol), n-butylamine (3.7 g, 50 mmol) and absolute ethanol (90 ml) were placed in a dry flask under a nitrogen atmosphere. This reaction mixture was stirred at 60° C. for 1 hour, cooled and adjusted to pH 3 using dry hydrogen chloride gas. The resulting white precipitate was filtered and the crystals washed with ice-cold ethanol/ether (1:1). The filtrate was concentrated to give a second crop of crystals. The combined yield of the hydroxylamine hydrochloride was 11.15 g, 99%, m.p. (sublimed) 150°. Analysis: (Found: C, 33.7; H. 2.2; Cl, 13.9; F, 37.8; N, 5.7, C7H5ClF5NO requires C, 33.7; H, 2.0; Cl, 14.2; F, 38.1; N, 5.6%). cooled The resulting white precipitate was filtered the crystals washed with ice-cold ethanol/ether (1:1) The filtrate was concentrated to give a second crop of crystals 11.15 g, 99%, m.p. (sublimed) 150°

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

Procedure: N-hydroxyphthalimide (8.15 g, 0.05 mol) was dissolved in a mixture of dry dimethoxyethane (40 ml) and dry dimethyl sulphoxide (10 ml). To this solution was added, in one portion, potassium carbonate (3.46 g, 0.05 mol). An orange suspension resulted. The pentafluorobenzyl bromide (10.8 g, 0.05 mol) in dry dimethoxyethane (10 ml) was added dropwise over 1 h at room temperature. The reaction mixture was stirred at room temperature for 64 h and then quenched by pouring into water (1 l). The resulting slurry was filtered, the crystals washed with water and dried in vacuo to give N-(pentafluorobenzyloxy)phthalimide as white crystals (15.9)g. An orange suspension resulted quenched by pouring into water (1 l) The resulting slurry was filtered the crystals washed with water dried in vacuo