Synthetic Route of 97456-81-0, The chemical industry reduces the impact on the environment during synthesis 97456-81-0, name is 1-Bromo-3-iodo-2-methylbenzene, I believe this compound will play a more active role in future production and life.
A solution of n-Bu3MgLi (6.6 mL of 0.66 M, 4.35 mmol) in hexane-heptane- dibutylether (8:20:3) is added to l-bromo-3-iodo-2-methyl-benzene (3.69 g, 12.42 mmol) in toluene (6.0 mL) and dibutylether (3.6 mL) at 0 C and stirred at the same temperature for 3.5 h. A solution of ZnBr2-LiBr in dibutyl ether (6.51 mL of 1.05 M, 6.83 mmol) is added dropwise, cooling bath removed and stirred at RT for 1 h. A solution of [(2R,3R,4S,5S,6R)-6- bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)tetrahydropyran-2-yl]methyl 2,2- dimethylpropanoate (6 g, 10.35 mmol, Ref. Sebastien Lemaire et. al. Org. Letts . 2012 , 14 , 1480-1483) in toluene (10.8 mL) is added, it is placed on pre-heated oil bath at 90 C and stirred for 24 h. The reaction mixture is cooled to RT and poured into aq. IN HC1 solution (80 mL), extracted with ethyl acetate (3 x 50 mL), combined extracts are washed with brine, dried (Na2S04) and concentrated. The residue is purified on Biotage SNAP 300 g silica gel cartridge using isocratic ethyl acetate in hexanes (10%, 4 CV) as eluent to afford title compound (4.5 g, 64.9%) as light yellow solid . 1H NMR (400 MHz, CDC13) delta 7.55 (d, J = 8.0 Hz, 1H), 7.49 (d, J = 7.7 Hz, 1H), 7.11 (t, J = 7.9 Hz, 1H), 5.71 – 5.65 (m, 1H), 5.43 (dd, J = 6.9, 2.8 Hz, 1H), 5.30 – 5.23 (m, 1H), 5.20 (d, J = 6.0 Hz, 1H), 4.68 – 4.58 (m, 1H), 4.07 (dd, J = 12.0, 3.1 Hz, 1H), 3.87 – 3.79 (m, 1H), 2.53 (s, 3H), 1.25 (s, 9H), 1.22 (s, 9H), 1.18 (s, 9H), 1.10 (s, 9H).
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, 1-Bromo-3-iodo-2-methylbenzene, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BENNANI, Youssef, Laafiret; CADILHAC, Caroline; DAS, Sanjoy, Kumar; DIETRICH, Evelyne; GALLANT, Michel; LIU, Bingcan; PEREIRA, Oswy, Z.; RAMTOHUL, Yeeman, K.; REDDY, T., Jagadeeswar; VAILLANCOURT, Louis; YANNOPOULOS, Constantin; VALLEE, Frederic; WO2013/134415; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com