Electric Literature of 128140-82-9, The chemical industry reduces the impact on the environment during synthesis 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, I believe this compound will play a more active role in future production and life.
Step 1) 1-((4-(Difluoromethoxy)phenyl)ethynyl)-3-methylbenzene To a solution of 3-bromophenylacetylene (2.5 g, 21.5 mmol), TEA (9.57 g, 94.6 mmol, 13.2 mL), bis(triphenylphosphine)dichloropalladium(II) (603 mg, 0.86 mmol), and CuI (98 mg, 0.516 mmol) in DMF (26 mL) was added 4-iodo(difluoromethoxy)benzene (4.64 g, 17.2 mmol) at room temperature. The reaction mixture had gotten warm after the addition was completed. The mixture was stirred for 4 h then the mixture was portioned between EtOAc and water. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated over 20 g Celite. Flash chromatography (SiO2, Hexanes) gave 2.4 g of a dark orange oil (component A) and 1.44 g of a dark red oil (component B). Flash chromatography of Component A (SiO2, Hexanes) and Component B (SiO2, Hexanes) separately yielded 3.2 g, 72%, of the title compound as a light peach oil. MS (+ESI): m/z 345 ([M+H]+). Step 1: 1-((4-(Difluoromethoxy)phenyl)ethynyl)-3-methylbenzene To a solution of 4-iodo(difluoromethoxy)benzene (4.64 g, 17.2 mmol) in DMF (26 mL) was added TEA (9.57 g, 13.2 mL, 94.6 mmol), PdCl2(PPh3)2 (603 mg, 0.86 mmol), CuI (98 mg, 0.516 mmol), and 3-ethynyltoluene (2.5 g, 2.78 mL, 0.90 mmol). The reaction mixture was stirred for 4 h then it was poured into water and diluted with EtOAc. The aqueous layer was separated and extracted twice more with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated onto 20 g Celite. Flash chromatography (SiO2, Hexanes) gave 1.44 g of a dark red oil and 2.44 g of a dark orange oil. Both fractions were rechromatographed, separately, to provide 3.2 g, 72%, of the title compound as a light peach oil. 1H NMR 500 MHz (CDCl3) delta 2.33 (s, 3H); 6.50 (t, J=73.6 Hz, 1H); 7.06 (d, J=8.81 Hz, 2H); 7.12 (d, J=6.83 Hz, 1H); 7.20 (d, J=7.53 Hz, 1H); 7.30 (d, J=7.76 Hz, 1H); 7.33 (s, 1H); 7.47-7.51 (m, 2H)
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, 1-(Difluoromethoxy)-4-iodobenzene, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com