Iodobenzene → 1-Phenyl-1,2,3-benzotriazole

Participants

Role	Name	HCID	Charge
Reactant	Iodobenzene	HCID 11575	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Reactant	HCID 178418385	HCID 178418385	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl acetate hexane	HCID 21226206	—
Product	1-Phenyl-1,2,3-benzotriazole	HCID 136693	95.3%

Reaction Steps

Using the general procedure, benzotriazole (0.119 g, 1.00 mmol) was coupled with iodobenzene (134 μL, 1.20 mmol) using CuI (9.5 mg, 0.050 mmol, 5.0 mol %), K3PO4 (2.1 mmol), trans-N,N′-dimethyl-1,2-cyclohexanediamine (16 μL, 0.10 mmol, 10 mol %) and dimethylformamide (1.0 mL) to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 9:1) provided 0.186 g (95% yield) of the product as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.17 (m, 1H), 7.78 (m, 3H), 7.62 (m, 2H), 7.55 (m, 2H), 7.42 (m, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09067955B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-88b68d9fa125494a8db4fca93e52a524
Source note	uspto-grants-2015_06