Electric Literature of 31827-94-8, 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. 31827-94-8, name is 2-Bromo-1-(4-iodophenyl)ethanone, This compound has unique chemical properties. The synthetic route is as follows.
Step A18b. A solution of the compound from step A18a (512 mg, 1.86 mmol) in (( (5 mL) was treated with DIPEA (0.45 mL, 2.58 mmol) and MsCl (0.16 mL, 2.07 mmol) for 2 hours at 0 C before being partitioned (CH2Cl2-water). The organics were washed with brine, dried ( a2S04), filtered and evaporated to give the crude desired compound as a colorless oil (725 mg), which was used directly in the next step. ESIMS m/z = 254.20 [M-Boc+2H]+. Step A18c. A solution of the compound from step A18b (1.82 mmol at most) in DMF (5 mL) was treated with 15-crown-5 (80 mg, 0.36 mmol) and al (1.36 g, 9.1 mmol) in the presence of K2CO3 (1.12 g, 8.12 mmol) at 90 C overnight before being cooled down and partitioned (EtO Ac -water). The organics were washed with water, brine, dried ( a2S04), filtered and evaporated. The residue was purified by chromatography (silica, hexanes- ethyl acetate) to give the desired compound as a colorless oil (396 mg, 56%) containing an isomeric impurity. ESIMS m/z = 386.10 [M+H]+. Step A18d. A solution of the compound from step A18c (516 mg, 1.34 mmol) in toluene (10 mL) was treated with totally 4 portions of Bu4SnH (0.36 mL, 1.34 mmol) and AIBN (22 mg, 0.134 mmol) for 12 hours at 110 C before being cooled down and evaporated. The residue was purified by chromatography (silica, hexanes-ethyl acetate) to give the desired compound as a colorless oil (177 mg, 51%) as a single isomer. ESIMS m/z = 260.10 [M+H]+. Step A18e. A solution of the compound from step A18d (170 mg, 0.655 mmol) in CH2CI2 (3 mL) was treated with DAST (0.18 mL, 1.32 mmol) at 0 C for 1 hours before being quenched with aqueous aHC03 dropwisely and partitioned (CH2Cl2-water). The organics were washed with brine, dried ( a2S04), filtered and evaporated. The residue was purified by chromatography (silica, hexanes-ethyl acetate) to give the desired compound as a colorless oil (177 mg, 51%). ESIMS m/z =260.10 [M+H]+. Step A18f. The desired compound was prepared from the compound from step A18e using procedures similar to that described in Intermediate A7. ESIMS m/z = 472.11 [M+H]+.
The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1-(4-iodophenyl)ethanone. I believe this compound will play a more active role in future production and life.
Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; NOVARTIS AG; QIU, Yao-ling; CAO, Hui; PENG, Xiaowen; GAO, Xuri; OR, Yat, Sun; SWEENEY, Zachary, Kevin; WO2015/17382; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com