4,4-DIFLUORO-1-PHENYL-1,3-BUTANEDIONE synthesis
- Product Name:4,4-DIFLUORO-1-PHENYL-1,3-BUTANEDIONE
- CAS Number:62679-61-2
- Molecular formula:C10H8F2O2
- Molecular Weight:198.17
Yield:62679-61-2 62%
Reaction Conditions:
with sodium hydride in tetrahydrofuran at 20; for 12 h;
Steps:
4.2. Synthesis of ligand
The ligand DPBD was synthesized and their synthetic route is illustrated in Scheme 1. To a solution of acetophenone (0.21 mL, 1.80 mmol) and dry THF (60 mL) added sodium hydride (0.70 g,2.90 mmol), the resulting mixture was stirred at room temperature for 15 min. Then added methyl-difluoroacetate (0.59 g, 5.40 mmol) and stirred the solution for 12 h at room temperature.The reaction mixture was evaporated till the solid residue was obtained. The residue was dissolved in dichloromethane (15 mL) then acidified with hydrochloric acid (0.5 M) and washed with water [19]. The solid residue was recrystalized from ethanol. The DPBD was obtained as dark brown solid in 62% yield with 47-51 °C melting point. IR (KBr): cm1 3430 (b), 3080 (m), 2998 (m), 2890(w), 1635 (s), 1542 (s), 1480 (s), 1360 (s), 1270 (s), 785 (s), 705 (s);1H NMR (400 MHz, CDCl3): d 15.01 (s, 1H, enolic OH), 7.45-7.22(m, 5H, Ar-H), 6.65 (t, 1H, CHF2), 6.35 (s, 1H, enol CH), 4.22 (s, 2H,keto-CH2) ppm.
References:
Bala, Manju;Kumar, Satish;Taxak;Boora, Priti;Khatkar [Journal of Fluorine Chemistry,2015,vol. 178,art. no. 8585,p. 6 - 13]
