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. 22385-77-9 name is 1-Bromo-3,5-di-tert-butylbenzene, 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. 22385-77-9
A solution of 2,2,6,6-tetramethylpiperidine (2.0 mL, 12 mmol) in THF (12 mL) was treated with n-BuLi (7.5mL, 1.60 M in hexane, 12 mmol) at 0 ¡ãC. After stirring for 1 h at 0 ¡ãC the solution wasadded to a solution of bromoferrocene (1.32 g, 5.00 mmol) in THF (10 mL) at ?78 ¡ãC.After stirring for 30 min at ?78 ¡ãC and 3 h at ?30 ¡ãC the reaction mixture wastransferred to a suspension of ZnCl2 (1.36 g, 10.0 mmol) in THF (10 mL) at ?78 ¡ãC.Stirring was continued at ?78 ¡ãC for 30 min before the mixture was warmed to roomtemperature, where stirring was maintained for 30 min. To the resulting solution wasadded a solution of 1-bromo-3,5-di-t-butylbenzene (1.48 g, 5.50 mmol) and [Pd(PPh3)4](0.29 g, 0.25 mmol) in THF (10 mL). The reaction mixture was heated to 60 ¡ãC for 10hours, before the reaction was quenched with a saturated aqueous ammonium chloridesolution. The reaction mixture was extracted with hexane and the combined organicphases were washed with water and dried over MgSO4. After filtration, the filtrate wasevaporated to dryness under reduced pressure and the obtained residue was purified bycolumn chromatography on silica gel (hexane) to give compound 3 (2.01 g, 4.43 mmol,89percent). 3: orange solid; m.p. 87?89 ¡ãC; 1H NMR (300 MHz, CDCl3) delta 1.37 (s, 18H), 4.17(s, 5H), 4.22 (t, J = 2.6 Hz, 1H), 4.43 (dd, J = 2.6, 1.4 Hz), 4.54 (dd, J = 2.6, 1.4 Hz),7.33 (t, J = 1.8 Hz, 1H), 7.55 (d, J = 1.8 Hz, 2H); 13C NMR (75 MHz, CDCl3) delta 31.6 (q),34.8 (q), 66.3 (d), 67.5 (d), 71.0 (d), 72.0 (d), 78.3 (s), 87.7 (s), 120.8 (d), 123.9 (d),135.2 (s), 149.8 (s). Anal. Calcd for C24H29BrFe: C, 63.60; H, 6.45percent. Found: C, 63.84;H, 6.48percent.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 22385-77-9, and friends who are interested can also refer to it.
Reference:
Article; Sasamori, Takahiro; Suzuki, Yuko; Sakagami, Michiyasu; Miyake, Hideaki; Tokitoh, Norihiro; Chemistry Letters; vol. 43; 9; (2014); p. 1464 – 1466;,
Bromide – Wikipedia,
bromide – Wiktionary