Reaktion #89187

Reaktionsgleichung

Cs2CO3

2-bromo-5-methylbenzoic acid

1,2,3-triazole

(1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine

→

title compound

Ausbeute 79.4%

5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

Ausbeute 79.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed
2. 2
   TemperaturThe reaction was cooled to rt
3. 3
   workup.ADDITIONdiluted with MeOH
4. 4
   SonstigeThe solvent was removed in vacuo
5. 5
   Sonstigeto obtain the crude which
6. 6
   Sonstigewas purified by silica gel chromatography (0˜100% DCM/EtOAc)

Vorschrift

A mixture of 2-bromo-5-methylbenzoic acid (2.0 g, 9.30 mmol), 1,2,3-triazole (1.08 mL, 18.6 mmol), (1S,2S)—N1,N2-dimethylcyclohexane-1,2-diamine (2.23 mL, 13.95 mmol), Cs2CO3 (4.55 g, 13.95 mmol) and CuI (124 mg, 0.65 mmol) in DMF (12 mL) was degassed and heated at 120° C. for 1 h in a microwave reactor. The reaction was cooled to rt, diluted with MeOH, and acidified with AcOH to pH 4-5. The solvent was removed in vacuo to obtain the crude which was purified by silica gel chromatography (0˜100% DCM/EtOAc) to yield the title compound as a yellow oil (1.5 g, 61%). MS (ESI) 204 (M+H).

Quelle