Reaction #157476

Reaction equation

sodium ascorbate

1-bromo-3-ethynylbenzene

azidomethyl 2,2-dimethylpropanoate

→

title compound

[4-(3-bromophenyl)-1H-1,2,3-triazol-1-yl]methyl 2,2-dimethylpropanoate

Solvents

t-BuOH water

water

water

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (×3)
2. 2
   WashCombined organics were washed (5% NH4OH, water, brine)
3. 3
   Dryingdried over Na2SO4
4. 4
   Concentrationconcentrated in vacuo

Procedure

To a mixture of 1-bromo-3-ethynylbenzene (0.430 g; 2.38 mmol; Note 1), and azidomethyl 2,2-dimethylpropanoate (0.391 g; 2.49 mmol; Note 2) in t-BuOH/water (3.5/3.0 mL respectively) at room temperature was added a solution of CuSO4.5H2O in water (0.030 g/0.5 mL), followed by sodium ascorbate (0.141 g; 0.71 mmol) in one portion. The mixture was stirred 25 h at room temperature, diluted with water and extracted with EtOAc (×3). Combined organics were washed (5% NH4OH, water, brine), dried over Na2SO4 and concentrated in vacuo affording the title compound as a tan solid which was used without further purification. LC/MS (method B) 2.77 min, m/z 338, 340 (M+H, Br isotopes).

Source