Réaction #91917

Équation de réaction

7-bromo-4-chromanone

2-methylphenylboronic acid

Na2CO3

→

title compound

7-(2-methylphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Solvants

dioxane

Conditions de réaction

Traitement

1. 1
   FiltrationThe mixture was filtered
2. 2
   Concentrationconcentrated
3. 3
   AutreThe residue was purified by silica gel chromatography (PE:EtOAc=10:1)

Mode opératoire

To a solution of 7-bromo-4-chromanone (2.0 g, 8.8 mmol) in dioxane (30 mL) was added 2-methylphenylboronic acid (1.8 g, 13.2 mmol), Pd(PPh3)4 (0.5 g, 0.44 mmol) and Na2CO3 (2.8 g, 26.4 mmol). The mixture was stirred at 100° C. under nitrogen overnight. The mixture was filtered and concentrated. The residue was purified by silica gel chromatography (PE:EtOAc=10:1) to give 2.1 g (quantitative) of the title compound as an off-white solid. 1H NMR (300 MHz, CDCl3): δ2.29 (s, 3H), 2.85 (t, J=6.3 Hz, 2H), 4.59 (t, J=6.3 Hz, 2H), 6.94 (s, 1H), 7.00 (d, J=8.1 Hz, 1H), 7.19-7.32 (m, 4H), 7.93 (d, J=8.1 Hz, 1H). [M+H] Calc'd for C16H14O2, 239. Found, 239.

Source