(4-methyl-3-methylsulfonylphenyl)methanamine

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

Procedure: A round bottom flask was charged with 4-(1-azidomethyl)-1-methyl-2-(methylsulfonyl)benzene (5.0 g, 22.17 mmol), THF (40 mL), triphenylphosphine (6.4 g, 24.3 mmol) and water (1.6 mL, 34.2 mmol) at 0° C., and the reaction mixture was stirred at room temperature over night. The solvents were removed and the residue was dissolved in MTBE and 20% HCl in dioxane was added dropwise at 0° C. and the resulting salt was collected and washed with EtOAc. The salt was then neutralized with 6N aq. NaOH and extracted with CH2Cl2. The organic layers were concentrated under reduced pressure to get the title compound as a very thick oil. 1H NMR (400 MHz, CDCl3): 7.98 (s, 1H), 7.50 (d, 1H, J=8.0 Hz), 7.32 (d, 1H, J=8.0 Hz), 3.93 (s, 2H), 3.08 (s, 3H), 2.69 (s, 3H). The solvents were removed the residue was dissolved in MTBE 20% HCl in dioxane was added dropwise at 0° C. the resulting salt was collected washed with EtOAc extracted with CH2Cl2 The organic layers were concentrated under reduced pressure