N-[(2,6-difluorophenyl)methylidene]hydroxylamine

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

Procedure: In a fashion similar to that for preparation 14, 2,6-difluorobenzaldehyde oxime (2.00 g, 12.7 mmol), N-chlorosuccinimide (1.75 g, 13.2 mmol), and DMF (20 ml) gave 2,6-difluorobenzoylchloride oxime (1.58 g, 65%) after column chromatography (silica gel, hexanes/diethyl ether gradient).

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

Procedure: In a fashion similar to that for preparation 13, 2,6-difluorobenzaldehyde (5.00 g, 35.2 mmol), hydroxylamine hydrochloride (2.93 g, 29.6 mmol), NaOH (7.04 g in 7.0 ml of water), ethanol (15 ml), water (15 ml), and ice (30 g) afforded 2,6-difluorobenzaldehyde oxime (5.13 g, 93%).

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

Procedure: In a fashion similar to that for preparation 14, 2,6-difluorobenzaldehyde oxime (2.00 g, 12.7 mmol), N-chlorosuccinimide (1.75 g, 13.2 mmol), and DMF (20 ml) gave 2,6-difluorobenzoylchloride oxime (1.58 g, 65%) after column chromatography (silica gel, hexanes/diethyl ether gradient).

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

Procedure: In a fashion similar to that for preparation 13, 2,6-difluorobenzaldehyde (5.00 g, 35.2 mmol), hydroxylamine hydrochloride (2.93 g, 29.6 mmol), NaOH (7.04 g in 7.0 ml of water), ethanol (15 ml), water (15 ml), and ice (30 g) afforded 2,6-difluorobenzaldehyde oxime (5.13 g, 93%).