Sodium Chloride → 2-Azido-1-(4-tert-butylphenyl)ethanone

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][CH:6]=1)=[O:4].[N-:15]=[N+:16]=[N-:17].[Na+].[Na+].[Cl-]>CC(C)=O>[N:15]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:7][CH:6]=1)=[O:4])=[N+:16]=[N-:17]

Participants

Procedure

To a solution of the product of Example 1A (985 mg, 3.86 mmol) in 45 mL acetone was added NaN3 (0.505 g, 7.07 mmol), and the mixture stirred overnight at room temperature. The reaction mixture was poured into saturated NaCl solution and extracted with dichloromethane. The extracts were washed with saturated NaCl solution, dried over Na2SO4, and concentrated in vacuo to afford the title compound as a yellow oil (715 mg, 85%). 1H NMR (DMSO-d6) δ 7.88 (d, 2H, J=8.5 Hz), 7.57 (d, 2H, J=8.5 Hz), 4.86 (s, 2H), 1.31 (s, 9H); MS (ESI+) m/z 218 (M+H).