Synthetic Route of 618-91-7, The chemical industry reduces the impact on the environment during synthesis 618-91-7, name is Methyl 3-iodobenzoate, I believe this compound will play a more active role in future production and life.
Substrate Compound 1 was arylated following the general arylation procedure A. Analysis of crude reaction mixture by XH NMR showed a > 20:1 ratio of mono- and diarylated products. After purification by column chromatography using hexane/EtOAc (5/1) as the eluent, Compound 21 was obtained as a white solid (50.0 mg, 88%). JH NMR (400 MHz, CDC13) delta 8.58 (br s, 1H) , 7.85-7.77 (m, 4H) , 7.75-7.70 (m, 2H) , 7.41-7.38 (m, 1H) , 7.30-7.26 (m, 1H) , 5.34 (dd, Ji = 6.0 Hz, J2 = 10.4 Hz, 1H), 3.80 (s, 3H) , 3.69 (ABqd, Jx = 6.2 Hz, J2 = 14.3 Hz, 1H) , 3.63 (ABqd, Ji = 10.4 Hz, J2 = 14.3 Hz, 1H) ; 13C NMR (100 MHz, CDC13) delta 167.9, 166.6, 166.4, 136.0, 134.7, 133.5, 131.0, 130.5, 130.0, 128.9, 128.6, 123.9, 56.2, 52.1, 34.9; HRMS (ESI-TOF) Calcd for C26Hi6F7N205 [M+H]+: 569.0942; found: 569.0941. Large scale reaction: Substrate Compound 1 (10 mmol, 4.34 g) , Pd(TFA)2 (1.0 mmol, 0.33 g) , and Ag2C03 (15 mmol, 4.14 g) were weighed in air and placed in a round-bottom flask (100 mL) with a magnetic stir bar. Methyl 3-iodobenzoate (15 mmol, 3.93 g) , 2-picoline (2.0 mmol, 0.19 g) , TFA (2.0 mmol, 0.23 g) , and DCE (35 mL) were added. The pressure vessel was sealed. The reaction mixture was first stirred at room temperature for 10 minuters and then heated to 100 C. Upon completion, the reaction mixture was purified by a silica gel-packed flash chromatography column, and Compound 21 was obtained in 78% yield (4.43 g) .
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, Methyl 3-iodobenzoate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; YU, Jin-Quan; WO2015/131100; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com