2-fluoro-5-methylsulfonylaniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Following the general method as outlined in Intermediate 76, starting from 1-chloro-2-nitro-4-[(trifluoromethyl)sulfonyl]benzene (MDA), the title compound was obtained as a brown solid in quantitative yield.

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

Procedure: A mixture of 4-fluoro-3-nitrophenyl methyl sulfone (Acros; 1.00 g; 4.56 mmol) and PtO2 (100 mg) in MeOH (150 ml) was placed in a PARR reactor and treated with a pressure of 20 atm of hydrogen for 3 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated to dryness affording the title compound (964 mg) as a dark green oil. was placed in a PARR reactor The reaction mixture was filtered through Celite the filtrate was concentrated to dryness

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Fluoro-5-(methylsulfonyl)aniline (Intermediate 57; 500 mg; 2.64 mmol) was treated with a 5 N solution of hydrochloric acid in water (8.98 ml; 44.92 mmol) and the solution cooled to 0° C. The solution was treated with sodium nitrite (219 mg; 3.17 mmol) and stirred at 0° C. for 30 minutes, then treated with a solution of potassium iodide (4.39 g; 26.43 mmol) in water (8 mL) and stirred at RT for 1 hour. EtOAc was added, the phases were separated and the organic phase was washed with a saturated sodium thiosulfate solution twice, then with brine. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give a residue which was purified by by flash column chromatography, eluting with cyclohexane containing increasing amounts of EtOAc. The title compound was obtained as a white solid. stirred at RT for 1 hour the phases were separated the organic phase was washed with a saturated sodium thiosulfate solution twice The organic phase was dried on MgSO4 filtered concentrated under reduced pressure to give a residue which was purified by by flash column chromatography eluting with cyclohexane containing increasing amounts of EtOAc

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

Procedure: A mixture of 4-fluoro-3-nitrophenyl methyl sulfone (ABCR; 1.50 g; 6.84 mmol) and 10% Pd/C (100 mg) in MeOH (30 ml) was placed in a PARR reactor and treated with a pressure of 15 atm of hydrogen for 2 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated to dryness affording the title compound (1.04 g, 80%). was placed in a PARR reactor The reaction mixture was filtered through Celite the filtrate was concentrated to dryness

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

Procedure: A mixture of 4-fluoro-3-nitrophenyl methyl sulfone (ABCR; 1.50 g; 6.84 mmol) and 10% Pd/C (100 mg) in MeOH (30 ml) was placed in a PARR reactor and treated with a pressure of 15 atm of hydrogen for 2 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated to dryness affording the title compound (1.04 g, 80%). was placed in a PARR reactor The reaction mixture was filtered through Celite the filtrate was concentrated to dryness

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

Procedure: A mixture of 4-fluoro-3-nitrophenyl methyl sulfone (ABCR; 1.50 g; 6.84 mmol) and 10% Pd/C (100 mg) in MeOH (30 ml) was placed in a PARR reactor and treated with a pressure of 15 atm of hydrogen for 2 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated to dryness affording the title compound (1.04 g, 80%). was placed in a PARR reactor The reaction mixture was filtered through Celite the filtrate was concentrated to dryness