Reference of 460-37-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, This compound has unique chemical properties. The synthetic route is as follows.
To zinc dust (3.24 g, 49.5 mmol, 3.41 eq) in a nitrogen-purged 40 mL vial with stir bar were added trimethylsilyl chloride (100 muL, 120 mg, 1.1 mmol, 8 mol %) and 1,2-dibromoethane (100 muL, 220 mg, 1.2 mmol, 8 mol %) by syringe. Anhydrous THF (16 mL) was added, followed by 1-iodo-3,3,3-trifluoropropane (3.8 g, 17.0 mmol, 1.17 eq) portionwise at RT with stirring over 20 min, keeping the exotherm below 50 C. The suspension was then stirred for 1 h at 50 C. To a separate 100 mL round bottom flask purged with nitrogen containing a stir bar were added RuPhos (655 mg, 1.40 mmol, 10 mol %), Pd2dba3 (629 mg, 0.687 mmol, 5 mol %), and DMF (20 mL). This was stirred for 30 min at 23 C. Trans-2-bromo-1-methylvinyl MIDA boronate (Aldrich cat. no. 763853, 3.79 g, 14.5 mmol, 1.00 eq) was then added to this solution in 13 mL DMF. The alkyl zinc suspension was filtered through a syringe filter and the filtrate was added to the DMF solution. The remaining alkylzinc solution was washed over with additional THF (2 mL). The reaction was then stirred for 24 h at 50 C., after which time nearly complete conversion of the vinyl bromide was observed by TLC (Cis plate, 2:1 H2O:MeCN, KMnO4 stain). In a separatory funnel, the reaction was diluted with EtOAc and saturated aqueous NH4Cl was added. The aqueous phase was extracted twice with EtOAc. The combined organic phase was washed three times with H2O, each time adding a few mL of brine to break the emulsion. The organic phase was dried with Na2SO4, concentrated to a dark orange foam, then dissolved in DCM and adsorbed onto celite. The celite pad was loaded onto a Cis silica column of 100 mL volume, eluting with a gradient of 30% to 60% MeCN in H2O. The product-containing fractions were combined and solid NaCl was added to induce phase separation. The organic phase was separated and the aqueous layer extracted with EtOAc (×2). The combined organic phases were dried and concentrated to give SI-10 as a yellow solid (2.91 g, 9.93 mmol 68% yield). (0225) 1H NMR (500 MHz, CDCl3) delta 5.87 (t, J=7.2 Hz, 1H), 3.81 (d, J=16.3 Hz, 2H), 3.69 (d, J=16.3 Hz, 2H), 2.79 (s, 3H), 2.41 (q, J=7.3 Hz, 2H), 2.27-2.14 (m, 2H), 1.68 (dt, J=1.6, 0.9 Hz, 3H). 13C NMR (126 MHz, CDCl3) delta166.90, 136.96, 61.77, 46.25, 33.06 (q, JC-F=27.7 Hz), 21.23 (q, JC-F=2.5 Hz), 14.39. 19F NMR (470 MHz, CDCl3) -66.33 (t, J=11.0 Hz). 11B NMR (128 MHz, CDCl3) delta 11.02. HRMS (ES+) Calculated for C11H16NO4BF3: 294.1124; Found: 294.1121.
The chemical industry reduces the impact on the environment during synthesis 1,1,1-Trifluoro-3-iodopropane. I believe this compound will play a more active role in future production and life.
Reference:
Patent; The Board of Trustees of the University of Illinois; BURKE, Martin D.; CROUCH, Ian; LEHMANN, Jonathan; PALAZZOLO, Andrea; SIMONS, Claire; US2018/305381; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com