Category: 345226-19-9

Synthetic Route of 345226-19-9,Some common heterocyclic compound, 345226-19-9, name is 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene, molecular formula is C7H3ClF3IO, 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.

To a mixture of 8-{[tert-butyl(dimethyl)silyl]oxy}-2-azaspiro[4.5]decan-1 -one (500 mg, 1 .76mmol) (isomer 1) and 3-chloro-4-iodophenyl trifluoromethyl ether (696 mg, 98% purity, 2.12mmol) in o-xylol (38 ml) was added under an argon atmosphere copper(l) iodide (67.2 mg, 353 pmol), N,N?-dimethylethylenediamine (77 pI, 710 pmol) and potassium phosphate (749 mg, 3.53 mmol) and the reaction was heated to 1400 for 48 h in a microwave reactor. Upon cooling, the reaction mixture was filtrated through a pad of celite the residue was washedwith ethyl acetate and the filtrate was concentrated under reduced pressure. Another batch was prepared accordingly, the batches were combined and the crude product was purified by flash chromatography (hexanes/ethyl acetate-gradient, 50% -> 100% ethyl acetate) to give the title compound as single isomer (1.0 g). [C-MS (Method 2): R = 1.78 mm; MS (ESipos): m/z = 478 [M+H]1H-NMR (400 MHz, DMSO-d6): 6 [ppm] = 7.71 (d, 1H), 7.62-7.36 (m, 2H), 3.94 (br 5, 1H),3.62 (t, 2H), 2.07 (t, 2H), 2.01-1.83 (m, 2H), 1.71-1.54 (m, 4H), 1.33 (brd, 2H), 0.88 (s, 9H),0.05 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 345226-19-9, 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. 345226-19-9, name is 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 2Methods of PreparationA. Synthesis of (6S)-6-[{2′-chloro-4′-(trifluoromethoxy)[1,1′-biphenyl]-4-yl]methoxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (1) by the method of Scheme 1 A stirred mixture of 4-(hydroxymethyl)phenylboronic acid (34) (308 mg, 2.03 mmol) and Pd(dppf)Cl2 (191 mg, 0.261 mmol) in toluene (22 mL) and EtOH (11 mL) was degassed for 8 min (vacuum pump) and then N2 was added. An aqueous solution of 2M Na2CO3 (4.4 mL, 8.8 mmol) was added by syringe and the stirred mixture was again degassed for 8 min, and then N2 was added. 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene (35) (585 mg, 1.81 mmol) was added by syringe and the resulting mixture was stirred at 88 C. for 60 min. The cooled mixture was then diluted with aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (5×100 mL). The extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-50% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 50% CH2Cl2/petroleum ether gave 2′-chloro-4′-(trifluoromethoxy)[1,1′-biphenyl]-4-yl]methanol (37) (537 mg, 98%) as a white solid: mp (pentane) 38-39 C.; 1H NMR (CDCl3) delta 7.46 (br d, J=8.2 Hz, 2H), 7.42 (dt, J=8.3, 2.0 Hz, 2H), 7.37 (br s, 1H), 7.36 (d, J=8.5 Hz, 1H), 7.19 (m, 1H), 4.77 (d, J=5.9 Hz, 2H), 1.70 (t, J=5.9 Hz, 1H); HREIMS calcd for C14H10ClF3O2 m/z (M+) 304.0292, 302.0321, found 304.0294, 302.0317.

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, 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Global Alliance for TB Drug Development; US2012/28973; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 345226-19-9, 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. 345226-19-9, name is 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

A stirred mixture of 4-(hydroxymethyl)phenylboronic acid (34) (308 mg, 2.03 mmol) and Pd(dppf)Cl2 (191 mg, 0.261 mmol) in toluene (22 mL) and EtOH (11 mL) was degassed for 8 min (vacuum pump) and then N2 was added. An aqueous solution of 2M Na2CO3 (4.4 mL, 8.8 mmol) was added by syringe and the stirred mixture was again degassed for 8 min, and then N2 was added. 2-Chloro-l-iodo-4-(trifluoromethoxy)benzene (35) (585 mg, 1.81 mmol) was added by syringe and the resulting mixture was stirred at 88 0C for 60 min. The cooled mixture was then diluted with aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (5x 100 mL). The extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-50% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 50% CH2Cl2/petroleum ether gave 2′-chloro-4′-(trifluoromethoxy)[l,r-biphenyl]-4-yl]methanol (37) (537 mg, 98%) as a white solid: mp (pentane) 38-39 C; 1H NMR (CDCl3) delta 7.46 (br d, J = 8.2 Hz, 2 H), 7.42 (dt, J = 8.3, 2.0 Hz, 2 H), 7.37 (br s, 1 H), 7.36 (d, J = 8.5 Hz, 1 H), 7.19 (m,I H), 4.77 (d, J = 5.9 Hz, 2 H), 1.70 (t, J = 5.9 Hz, 1 H); HREIMS calcd for C14H10ClF3O2 mlz (M+) 304.0292, 302.0321 , found 304.0294, 302.0317.

The chemical industry reduces the impact on the environment during synthesis 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT; DENNY, William, Alexander; THOMPSON, Andrew, M.; BLASER, Adrian; MA, Zhenkun; PALMER, Brian, Desmond; SUTHERLAND, Hamish, Scott; KMENTOVA, Iveta; WO2011/14774; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com