(NE)-N-[(4-fluorophenyl)methylidene]hydroxylamine

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

Procedure: To a stirred solution of N-chlorosuccinimide (0.53 g, 4.00 mmol) in methylene chloride (20 mL) was added syn-4-fluorobenzaldoxime (0.56 g, 4.00 mmol) in one portion. The resulting mixture was stirred at room temperature for 3 hours. Propargyl acetate (0.10 g, 1.00 mmol) was then added in one portion, followed by triethylamine (0.28 mL, 2.00 mmol) in methylene chloride (5 mL) over a period of 20 min. The resulting mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue was purified by prep-TLC (ethyl acetate:hexanes=1:4) to give [3-(4-fluorophenyl)isoxazol-5-yl]methyl acetate. The resulting mixture was stirred at room temperature overnight The solvent was removed under reduced pressure the residue was purified by prep-TLC (ethyl acetate:hexanes=1:4)

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

Procedure: To a stirred solution of N-chlorosuccinimide (0.53 g, 4.00 mmol) in methylene chloride (20 mL) was added syn-4-fluorobenzaldoxime (0.56 g, 4.00 mmol) in one portion. The resulting mixture was stirred at room temperature for 3 hours. Propargyl acetate (0.10 g, 1.00 mmol) was then added in one portion, followed by triethylamine (0.28 mL, 2.00 mmol) in methylene chloride (5 mL) over a period of 20 min. The resulting mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue was purified by prep-TLC (ethyl acetate:hexanes=1:4) to give [3-(4-fluorophenyl)isoxazol-5-yl]methyl acetate. The resulting mixture was stirred at room temperature overnight The solvent was removed under reduced pressure the residue was purified by prep-TLC (ethyl acetate:hexanes=1:4)

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

Procedure: To a stirred solution of N-chlorosuccinimide (0.53 g, 4.00 mmol) in methylene chloride (20 mL) was added syn-4-fluorobenzaldoxime (0.56 g, 4.00 mmol) in one portion. The resulting mixture was stirred at room temperature for 3 hours. Propargyl acetate (0.10 g, 1.00 mmol) was then added in one portion, followed by triethylamine (0.28 mL, 2.00 mmol) in methylene chloride (5 mL) over a period of 20 min. The resulting mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the residue was purified by prep-TLC (ethyl acetate:hexanes=1:4) to give [3-(4-fluorophenyl)isoxazol-5-yl]methyl acetate. The resulting mixture was stirred at room temperature overnight The solvent was removed under reduced pressure the residue was purified by prep-TLC (ethyl acetate:hexanes=1:4)