Electric Literature of 33406-96-1, The chemical industry reduces the impact on the environment during synthesis 33406-96-1, name is 1-Chloro-4-fluoro-2-methylbenzene, I believe this compound will play a more active role in future production and life.
General procedure: Example 3Tandem Borylation/Dehalogenation of 1-Chloro-4-fluoro-3-Substituted- and 1-Bromo-4-fluoro-3-Substituted BenzenesTandem borylation/dehalogenation was also investigated as a strategy for the ortho-borylation of arenes that are substituted with an electron-withdrawing group. The scheme below illustrates the tandem borylation/dehalogenation methodology which was investigated. As discussed above, in the case of arenes that are substituted with an electron-withdrawing group, iridium-catalyzed C-H activation-borylation of the arene is typically governed by steric effects. In tandem borylation/dehalogenation, the substrate can include an electron-withdrawing group and a sacrificial atom (e.g., a halogen such as Cl or Br) positioned para to the electron-withdrawing group, so as to sterically hinder attack of the iridium catalyst at the otherwise sterically favored position meta to the electron-withdrawing group. As a result, iridium-catalyzed C-H activation-borylation of the arene exclusively generates the ortho-borylated (electronic) product. Subsequent dehalogenation can afford exclusively the desired electronic product.[0337] General Procedure for Borylation [0338] In a nitrogen atmosphere glovebox B2Pin2 (140 mg, 0.55 mmol) was weighed into a 20 mL vial containing a magnetic stir bar. [Ir(OMe)cod]2 (6.6 mg, 0.02 mmol) and 4,4?-di-tert-butyl-2,2?-dipyridyl ligand (5.4 mg, 0.02 mmol) were weighed into two separate test tubes, each being diluted with THF (2 mL). The [Ir(OMe)cod]2 solution was transferred into the 20 mL vial containing B2Pin2. This mixture was stirred until a golden yellow clear solution was obtained. The solution containing ligand was transferred into the vial, and the mixture was stirred until it became a dark brown color solution. The substrate (1 mmol) was added to the vial, which was then sealed. The reaction mixture stirred for 24 h at rt, after which the vial was removed from the glovebox. The reaction mixture was passed through a short plug of silica eluting with a 10:1 hexane/EtOAc solution (2¡Á10 mL). The volatiles were removed by rotary evaporation affording the product, which was characterized using standard methodologies. 1-Chloro-4-fluoro-2-methylbenzene was borylated using the general procedure described above. After workup, a white solid was obtained (2.38 g, 88%): mp 48-49 C.; 1H NMR (500 MHz, CDCl3) delta 7.66 (d, J=5.5 Hz, 1H), 6.91 (d, J=9.5 Hz, 1H), 2.35 (s, 3H), 1.34 (s, 12H); 13C NMR (125 MHz, CDCl3) delta 165.4 (d, J=249.4 Hz), 141.7 (d, J=9.5 Hz), 136.5 (d, J=8.5 Hz), 129.1 (d, J=2.9 Hz), 117.7 (d, J=25.6 Hz), 84.1, 24.7, 20.4 (d, J=1.9 Hz); 19F NMR (470 MHz, CDCl3) delta 106.5; 11B NMR (160 MHz, CDCl3) delta 29.8 (br s).
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-Chloro-4-fluoro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; Smith, III, Milton R.; Maleczka, JR., Robert E.; Li, Hao; Jayasundara, Chathurika; Oppenheimer, Jossian; Sabasovs, Dmitrijs; US2015/65743; (2015); A1;,
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