Reference of 129316-09-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 129316-09-2 name is 1,3-Dibromo-5-(tert-butyl)benzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
General procedure: [00826] Synthesised according to general procedures GP1 1 – from i) 1 ,3-dibromo-5-(fe/f- butyl)benzene (2.0 g, 6.85 mmol), ‘BuLi (1 .6 M in pentane; 8.5 ml_, 13.6 mmol), THF (70 mL and 5 ml_), dimethyl disulfide (0.74 mL, 8.22 mmol); -78 C?rt; chromatography (EtOAc/cyclohexane 0?10%), 1 .50 g, 85%. ii) (3-bromo-5-(te/ -butyl)phenyl)(methyl)sulfane (1 .50 g, 5.79 mmol), m-CPBA (77%; 2.50 g, 1 1 .1 mmol), DCM (50 mL); rt, 12 h; chromatography (EtOAc/cyclohexane 0?30%), 1 .40 g, 83%. NMR (500 MHz, CDCI3) delta 7.87 (t, J = 1 .6 Hz, 1 H), 7.85 (t, J = 1 .6 Hz, 1 H), 7.76 (t, J = 1 .7 Hz, 1 H), 3.05 (s, 3H), 1 .32 (s, 9H). General procedures GP11 (1119) [00687] ‘BuLi was added dropwise over 20 min to a solution of 1 ,3-dibromo-5-(fe/?-butyl)benzene in THF at -78 C and stirring was maintained at -78 C for 10 min. A solution of disulfide (RSSR) in THF was added dropwise over 20 min at the same temperature and the reaction was warmed slowly to rt. Sat. NH4CI was added. The aqueous phase was extracted with EtOAc (3 x). The combined organic phase was dried over MgSC , filtered and the solvent was removed under reduced pressured. The crude was purified by chromatography (1120) [00688] m-CPBA was added in small portions to a solution of the intermediate sulfide in DCM. The mixture was stirred at rt for 12 h and diluted with EtOAc. The solution was washed with sat. NaHCC (3 x), dried over MgSC , filtered and the solvent was subsequently removed under reduced pressure. The crude was purified by chromatography
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-(tert-butyl)benzene, and friends who are interested can also refer to it.
Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; SPRINGER, Caroline; MARAIS, Richard; NICULESCU-DUVAZ, Dan; LEUNG, Leo; SMITHEN, Deborah; CALLENS, Cedric; TANG, Haoran; (403 pag.)WO2017/141049; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary