2-azido-1-(4-fluorophenyl)ethanone

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 2-azido-1-(4-fluoro-phenyl)-ethanone (8.0 g, 44.7 mmol) in ethanol (125 mL) was added concentrated aqueous HCl (6 mL) and 10% Pd/C (10 mol %). The mixture was stirred under hydrogen (H2) atmosphere at 45 psi for 1 hour. The mixture was filtered through celite and the celite cake was washed with copious amounts of methanol. The solvent was under reduce pressure and the semisolid was triturated with diethyl ether, filtered and dried to give 2-amino-1-(4-fluoro-phenyl)-ethanone hydrochloride (5.0 g, 26.5 mmol) as a white crystalline solid. The mixture was filtered through celite the celite cake was washed with copious amounts of methanol the semisolid was triturated with diethyl ether filtered dried

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

Procedure: A solution of 2-bromo-1-(4-fluoro-phenyl)-ethanone (2.5 g, 11.5 mmol) in DMSO (15 mL) at 10° C. was vigorously stirred and sodium azide (0.94 g, 14.4 mmol) was added. The mixture was stirred for I hour then quenched with water (20 mL) and extracted with ethyl acetate (2×25 mL). The combined organic layers were washed with water (25 mL) and brine (25 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduce pressure to give 2-azido-1-(4-fluoro-phenyl)-ethanone (1.7 g, 9.3 mmol) as a viscous yellow-red liquid. then quenched with water (20 mL) extracted with ethyl acetate (2×25 mL) The combined organic layers were washed with water (25 mL) and brine (25 mL) dried over anhydrous sodium sulfate filtered concentrated

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

Procedure: A solution of 2-bromo-1-(4-fluoro-phenyl)-ethanone (2.5 g, 11.5 mmol) in DMSO (15 mL) at 10° C. was vigorously stirred and sodium azide (0.94 g, 14.4 mmol) was added. The mixture was stirred for I hour then quenched with water (20 mL) and extracted with ethyl acetate (2×25 mL). The combined organic layers were washed with water (25 mL) and brine (25 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduce pressure to give 2-azido-1-(4-fluoro-phenyl)-ethanone (1.7 g, 9.3 mmol) as a viscous yellow-red liquid. then quenched with water (20 mL) extracted with ethyl acetate (2×25 mL) The combined organic layers were washed with water (25 mL) and brine (25 mL) dried over anhydrous sodium sulfate filtered concentrated

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

Procedure: A solution of 2-bromo-1-(4-fluoro-phenyl)-ethanone (1 eq) in DMSO at 10° C. is vigorously stirred and sodium azide (1.25 eq) is added. The mixture is stirred for 1 hour then quenched with water and extracted with ethyl acetate (2×). The combined organic layers are washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduce pressure to give 2-azido-1-(4-fluoro-phenyl)-ethanone. then quenched with water extracted with ethyl acetate (2×) The combined organic layers are washed with water and brine dried over anhydrous sodium sulfate filtered concentrated

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

Procedure: To a solution of 2-azido-1-(4-fluoro-phenyl)-ethanone in ethanol is added concentrated HCl (aq) and 10% Pd/C (10 mol %). The mixture is stirred under hydrogen (H2) atmosphere at 45 psi for 1 hour. The mixture is filtered through celite and the celite cake is washed with copious amounts of methanol. The solvent is removed under reduce pressure and the resulting residue is triturated with diethyl ether, filtered and dried to give 2-amino-1-(4-fluoro-phenyl)-ethanone hydrochloride. The mixture is filtered through celite the celite cake is washed with copious amounts of methanol The solvent is removed the resulting residue is triturated with diethyl ether filtered dried