Synthetic Route of 685-88-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 685-88-1, name is Diethyl fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
NaH (0.88 g, 22 mmol 60% in mineral oil) was washed free from the oil with hexanes (3 × 10 mL) and was suspended in dry DMF (30 mL). Diethyl fluoromalonate (2.85 g, 16 mmol) dissolved in dry DMF (10 mL) was added dropwise while cooled in ice. After stirring for 10 minutes, 1-fluoro-2-nitrobenzene (2.10 g, 15 mmol) in dry DMF (10 mL) was added and the mixture was heated to 90 C for 18 hours. After cooling to room temperature, the mixture was poured into water (300 mL), acidified with concentrated HCl (2 mL) and extracted with ether (3 × 70 mL). The combined extracts were washed with saturated NaHCO3 solution (2 × 50 mL) and brine (1 × 50 mL) and dried over Na2SO4. After evaporation of the solvent under reduced pressure an orange oil was obtained that was purified by Kugelrohr distillation (8 mbar, 200 C) to afford diethyl 2-fluoro-2-(2-nitrophenyl)malonate (3, 3.21 g, 71%) as an orange solid. M.p. 48-49 C; IR (neat, cm-1) 2996, 1755, 1530, 1276, 1103; deltaH (CDCl3, 400 MHz) 1.33 (6H, t, J 7.1, CH3), 4.31 – 4.43 (4H, m, CH2), 7.57 – 7.63 (2H, m, Ar-H), 7.66 – 7.71 (1H, m, Ar-H), 8.04 (1H, d, J 8.0, Ar-H); deltaF (CDCl3, 376 MHz) – 152.98 (s, C-F); deltaC (CDCl3, 100 MHz) 14.01 (s, CH3), 63.55 (s, CH2), 94.05 (d, 1JCF 198.7, C-F), 125.87 (s, Ar), 128.54 (s, Ar), 128.66 (s, Ar), 128.89 (s, Ar), 130.97 (s, Ar), 133.30 (s, Ar), 164.68 (d, 2JCF 25.1, COO); m/z (ASAP): 226.0 (85%, [M-CO2Et]+), 134.0 (100%).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Diethyl fluoromalonate, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Harsanyi, Antal; Sandford, Graham; Yufit, Dmitri S.; Howard, Judith A.K.; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1213 – 1219;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics