Réaction #48332

Équation de réaction

HCl

malonic acid

(Z)-N-(6-bromo-2-(trifluoromethyl)-4H-chromen-4-ylidene)(phenyl)methanamine

water

EtOH H2O

→

title compound

6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-one

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureto reflux for 18 h until the reaction
3. 3
   workup.WAITThe resulted mixture was left
4. 4
   ExtractionThe product was extracted with hexane (3×300 ml)
5. 5
   Séchagedried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   AutreThe residue was purified on silica gel column (2-10% EtOAc/hexane)

Mode opératoire

A mixture of malonic acid (1.2 ml, 19 mmol) and (Z)-N-(6-bromo-2-(trifluoromethyl)-4H-chromen-4-ylidene)(phenyl)methanamine (6.63 g, 17 mmol) in dioxane was heated to reflux for 18 h until the reaction was completed. The mixture was cooled to RT and treated with 50% EtOH/H2O (20 ml) followed by conc. HCl (5.0 ml). The resulted mixture was left to stand at RT for 40 min, and then diluted with water (500 ml). The product was extracted with hexane (3×300 ml). The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column (2-10% EtOAc/hexane) to afford the title compound as yellow oil. MS m/z: 310 (M+1).

Source