These common heterocyclic compound, 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, its 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. Product Details of 31599-61-8
Substrate 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 toluene/EtOAc (30/1) as the eluent, Compound 2r was obtained as a white solid (47.0 mg, 87%). 1H NMR (600 MHz, CDC13) delta 8.44 (br s, 1H) , 7.83-7.80 (m, 2H) , 7.75-7.72 (m, 2H) , 6.97-6.96 (m, 2H) , 6.94-6.92 (m, 1H) , 5.31 (dd, sigma = 6.6 Hz, J2 = 10.2 Hz, 1H) , 3.58 (ABqd, J = 6.6 Hz, J2 = 14.4 Hz, 1H) , 3.48 (ABqd, Jj. = 10.2 Hz, J2 = 14.4 Hz, 1H) , 2.14 (s, 3H) , 2.11 (s, 3H) ; 13C NMR (150 MHz, CDC13) 5168.1, 166.7, 137.2, 135.7, 134.6, 132.7, 131.2, 130.13, 130.09, 126.1, 123.8, 56.6, 34.9, 19.5, 19.3; HRMS (ESI-TOF) Calcd for C26HIBF7N203 [M+H] + : 539.1200; found: 539.1195. Large scale reaction: Substrate Compound 1 (15 mmol, 6.51 g) , Pd(TFA)2 (1.5 mmol, 0.50 g) , and Ag2C03 (22.5 mmol, 6.12 g) were weighed in air and placed in a round-bottom flask (100 inL) with a magnetic stir bar. 4-Iodo-o-xylene (22.5 mmol, 5.22 g), 2-picoline (3.0 mmol, 0.28 g) , TFA (3.0 mmol, 0.34 g) , and DCE (50 mL) were added. The pressure vessel was sealed. The reaction mixture was first stirred at room temperature for 10 minutes and then heated to 100 C. Upon completion, the reaction mixture was purified by a silica gel-packed flash chromatography column, and Compound 2r was obtained in 79% yield (6.38 g) .
The synthetic route of 4-Iodo-1,2-dimethylbenzene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; YU, Jin-Quan; WO2015/131100; (2015); A1;,
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