Water → 1-(4-Chloro-3-(methylsulfonyl)phenyl)ethanamine

Reaction equation

[N:1]([CH:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:7]=1)[CH3:5])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([CH:4]([NH2:1])[CH3:5])=[CH:7][C:8]=1[S:13]([CH3:16])(=[O:14])=[O:15]

Participants

Procedure

A round bottom flask was charged with 4-(1-azidoethyl)-1chloro-2-(methylsulfonyl)benzene (2.1 g, 7.7 mmol), THF (20 mL), triphenylphosphine (2.4 g, 8.5 mmol) and water (0.6 mL, 34.2 mmol) at 0° C. and the reaction 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. The resulting salt was collected and washed with EtOAc. The salt was then neutralized with 6N NaOH and extracted with CH2Cl2. The combined organic layers were concentrated under reduced pressure to get the title compound as a very thick oil. 1H NMR (400 MHz, CDCl3): 8.14 (d, 1H, J=2.0 Hz), 7.63 (dd, 1H, J=8.4, 2.4 Hz), 7.52 (d, 1H, J=8.0 Hz), 4.24 (q, 1H, J=6.4 Hz), 3.28 (s, 3H), 1.40 (d, 3H, J=6.4 Hz).