Electric Literature of 90347-66-3, 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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.
A suspension of 4-methylimidazole (1, 3.0 g, 36 mmol), 2 (4.8 g, 20 mmol), K2CO3(4.5 g, 33 mmol), CuI (1.14 g, 6 mmol) and 8-hydroxyquinoline (0.56 g, 4 mmol) in DMSO(20 mL) was heated at 120 C overnight under nitrogen. After cooling, water was added andthe mixture was extracted with EtOAc twice. The combined organic layers were washed withbrine, dried over Na2SO4 and concentrated. The residue was purified by silica gel columnchromatography to give 3 (2.8 g, 58%) as a yellow solid. LCMS (m/z: m+1): 242.2. A mixtureof 4 (7.26 g, 26.3 mmol), 5 (3.0 g, 17.5 mmol), K2CO3 (4.84 g, 35.0 mmol), DMEDA (386 mg,4.38 mmol) and CuI (834 mg, 0.871 mmol) in 90 ml of dioxane was stirred at 100 C under N2for 18h. The mixture was filtered, concentrated and purified by column chromatography to give6 (2.2 g, 39%) as a slightly yellow solid. LCMS (m/z: m+1): 320.2. To a solution of 6 (2.2 g,6.89 mmol) in THF/water (60/30 mL) was added LiOH (496 mg, 20.7 mmol). The reactionwas stirred at room temperature overnight, concentrated. To the residue water (30 ml) wasadded and then acidified to pH 4 with aqueous KHSO4. The precipitate was filtered and washedwith water and EtOAc. The cake was collected and dried to give 7 (1.4 g, 67%) as a whitesolid. LCMS: m/z: (M+1): 306. To a solution of 7 (100 mg, 0.33 mmol) in NMP (2 mL) wasadded SOCl2 (58 mg, 0.49 mmol). The reaction was heated at 90 C for 1 hour before 3 (80mg, 0.33 mmol) was added. The resulting mixture was stirred at 90 C for 3 hours. The reactionwas quenched with water and basified with aqueous NaOH. The mixture was extracted withEtOAc twice. The combined organic layers were washed with brine, dried over Na2SO4 andconcentrated. The residue was purified by reverse prep-HPLC and then silica gel prep-TLC togive 1a (22 mg, 13%) as a white solid.
The chemical industry reduces the impact on the environment during synthesis Methyl 3-iodo-4-methylbenzoate. I believe this compound will play a more active role in future production and life.