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0 °C

A cooled (0° C.) solution of 2-methyl-5-(methylsulfonyl)aniline (Intermediate 16; 556 mg; 3.00 mmol) in aqueous hydrogen chloride (5 M, 10 mL; 50 mmol) was treated with sodium nitrite (248 mg; 3.60 mmol) and the resulting mixture was stirred at 0° C. for 30 minutes, before being treated with a solution of potassium iodide (4.98 g; 30 mmol) in water (8 mL). The resulting mixture was stirred at RT for 1 hour, the EtOAc was added and the phases separated. The organic layer was washed twice with an aqueous, saturated sodium thiosulfate solution, then with brine, dried over MgSO4 and concentrated to afford a residue which was purified by column chromatography, eluting with cyclohexane containing increasing amounts of EtOAc to afford the title compound (649 mg, 73%) as a colorless liquid.

1. stirringThe resulting mixture was stirred at RT for 1 hour
2. customthe phases separated
3. washThe organic layer was washed twice with an aqueous, saturated sodium thiosulfate solution
4. dry with materialwith brine, dried over MgSO4
5. concentrationconcentrated
6. customto afford a residue which
7. customwas purified by column chromatography
8. washeluting with cyclohexane containing
9. temperatureincreasing amounts of EtOAc