Synthetic Route of 364-75-0, A common heterocyclic compound, 364-75-0, name is 1-Fluoro-4-iodo-2-nitrobenzene, molecular formula is C6H3FINO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
The synthesis was carried out following a known procedure (Serizawa et al., ?Direct Synthesis of Pentafluoroethyl Copper from Pentafluoropropionate as an Economical C2F5 Source: Application to Pentafluoroethylation of Arylboronic Acids and Aryl Bromides,? Org. Lett. 16:3456-3459 (2014), which is hereby incorporated by reference in its entirety). A 25 mL Schlenk flask (equipped with a 10 mL solid addition funnel) was flame-dried under vacuum and cooled under Ar. The flask was charged with copper(I) chloride (516 mg, 5.21 mmol; transferred in an Ar-purged glove bag) and DMF (18 mL). Sodium tert-butoxide (1.01 g, 10.4 mmol; transferred in a glove bag) was added via the addition funnel in portions over 10 mm. After replacing the addition funnel with a septum, the mixture was stirred at room temperaturefor 2.5 hours, and then was heated at 50C while ethyl 2,2,3,3,3-pentafluoropropanoate (770 jiL,5.21 mmol) was added dropwise by syringe over 2-3 mm. The reaction was stirred at 50C for 3 hours and then was cooled to 0C. Triethylamine trihydrofluoride (325 jiL, 1.99 mmol) was added dropwise over 1-2 mm by syringe, which resulted in a nearly homogeneous solution. Stirring was continued at 0C for 5 mm, and then at room temperature for 15 mm. Solid 1-fluoro-4-iodo-2-nitrobenzene (662 mg, 2.48 mmol) was added in one-portion and the reaction was heated at 80C for 12 hours, under a balloon of Ar. After the reaction had cooled to room temperature, 1 M HC1 (15 mL) was added in portions over 1-2 mm by pipet. The mixture was diluted with water (50 mL) and Et20 (50 mL), and then was filtered through a pad (3 x 3 cm) of Celite under vacuum. The filter-cake was washed with Et20 (20 mL) and the combined filtrateswere transferred to a separatory funnel. The layers were separated and the aqueous phase was extracted with Et20 (2 x 30 mL). The organic extracts were pooled, washed with a 60:40 mixture of saturated NH4C1 solution/concentrated NH4OH solution (3 x 50 mL), half saturated NaC1 solution (2 x 50 mL) and brine (50 mL), dried (Mg504), and filtered. Concentration under vacuum gave 670 mg of an orange oil, which was used without further purification (seesynthesis of APS5-1 1).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; ICHAN SCHOOL OF MEDICINE AT MOUNT SINAL; DAR, Arvin, C.; CAGAN, Ross, L.; SCOPTON, Alex, P.; SONOSHITA, Masahiro; (175 pag.)WO2018/35346; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com