ChemicalBook CAS DataBase List 5-BENZO[1,3]DIOXOL-5-YL-2H-TETRAZOLE

5-BENZO[1,3]DIOXOL-5-YL-2H-TETRAZOLE synthesis

5synthesis methods

Product Name:5-BENZO[1,3]DIOXOL-5-YL-2H-TETRAZOLE
CAS Number:118923-32-3
Molecular formula:C8H6N4O2
Molecular Weight:190.16

2089-36-3 Synthesis

2089-36-3
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$47.70/5g

118923-32-3
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$495.23/5MG

Yield:118923-32-3 353.7 mg

Reaction Conditions:

with diphenylphosphoranyl azide;1,8-diazabicyclo[5.4.0]undec-7-ene in toluene at 110;Inert atmosphere;

Steps:

4.1 4.2. Typical experimental procedure for preparation of 5-aryltetrazoles 3 from aryl bromides 1

General procedure: n-BuLi (1.55 M solution in hexane, 2.32 mL, 3.6 mmol) was added dropwise to a solution of 4-methylphenyl bromide (513 mg, 3.0 mmol) in THF (6.0 mL) at -50 °C under Ar atmosphere. After 30 min, DMF (278 μL, 3.6 mmol) was added and the obtained mixture was gradually warmed to r.t. After 1 h at the same temperature, NH₂OHxHCl (313 mg, 4.5 mmol) and K₂CO₃ (622 mg, 4.5 mmol) were added and the obtained mixture was stirred for 2 h at r.t. Then, after removal of the solvent under reduced pressure, toluene (3.0 mL), DPPA (1.61 mL, 7.5 mmol), and DBU (1.57 mL, 10.5 mmol) were added to the obtained residue under Ar atmosphere. After being stirred for 16 h under refluxing conditions, the mixture was cooled to r.t. and then, saturated NaHCO₃ aq. (15.0 mL) was added. After being stirred for 5 min, the mixture was diluted with water (5.0 mL). The aqueous layer was then washed with AcOEt (25.0 mL) and acidified with 1.0 M HCl aq. to pH 2. The aqueous layer was extracted with AcOEt (2 x 25.0 mL). Removal of the solvent, followed by purification of the residue by short column chromatography on neutral silica gel (AcOEt: hexane = 1:3-1:1) gave 5-(4′-methylphenyl)tetrazole 3A (336.1 mg, 70%).

References:

Kobayashi, Eiji;Togo, Hideo [Tetrahedron,2018,vol. 74,# 31,p. 4226 - 4235]