Electric Literature of 39998-81-7, 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. 39998-81-7, name is 2-Fluoro-4-iodo-1-methylbenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
Preparation of 1-(2-fluoro-4-iodobenzyl)-4-ethyl-2-propyl-1H-imidazole-5-carboxaldehyde A solution of 2-fluoro-4-iodotoluene (47.28 g, 0.20 mol), N-bromosuccinamide (37.64 g, 0.21 mol) and azobisisobutyronitrile (3.65 g, 0.02 mol) in CCl4 (200 mL) was refluxed under N2 overnight. The mixture was cooled, the solid was filtered off and washed with CCl4. The filtrate was concentrated. The precipitated formed was filtered and washed with hexane to give 13.92 g of 86% pure benzyl bromide. The mother liquid was concentrated to give 48.88 g of 60% pure benzyl bromide. Both fractions were used without further purification in the next step. 4-Ethyl-2-propyl-1H-imidazole-5-carboxaldehyde (6.32 g, 38.0 mmol), potassium carbonate (10.57 g, 76.5 mmol), and 2-fluoro-4-iodobenzyl bromide (13.90 g of 86%, 38.0 mmol) were added together with 50 mL of DMF. The reaction mixture was stirred at room temperature overnight under N2. The solvent was removed in vacuo and the residue was partitioned between EtOAc and H2 O. The two layers were separated. The aqueous layer was extracted with EtOAc. The combined organic mixture was washed with H2 O and brine, dried over MgSO4 and concentrated. The crude product mixture was purified by flash chromatography (silica gel, 30-50% EtOAc/hexane) to yield 10.63 g orange oil (70%). MS m/e 401.0, [M+H]+; 1 H NMR (300 MHz, CDCl3): delta0.95 (t, 3H, CH3), 1.32 (t, 3H, CH3), 1.70 (m, 2H, CH2), 2.60 (m, 2H, CH2), 2.82 (q, 2H, CH2), 5.52 (s, 2H, CH2 Ar), 6.42 (t, 1H, ArH), 7.38 (d, 1H, ArH), 7.42 (d, 1H, ArH), 9.73 (s, 1H, CHO).
The synthetic route of 2-Fluoro-4-iodo-1-methylbenzene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; The Du Pont Merck Pharmaceutical Company; US5395844; (1995); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com