Synthetic Route of 22385-77-9, These common heterocyclic compound, 22385-77-9, name is 1-Bromo-3,5-di-tert-butylbenzene, 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.
A solution of2,2,6,6-tetramethylpiperidine (1.6 mL, 9.6 mmol) in THF (10 mL) was treated withn-BuLi (6.0 mL, 1.60 M in hexane, 9.6 mmol) at 0 ¡ãC. After stirring for 1 h at 0 C thesolution was added to a solution of compound 3 (1.81 g, 4.00 mmol) in THF (8 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 (1.09 g, 8.00 mmol) in THF (8 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 (1.18 g, 4.40 mmol) and [Pd(PPh3)4](0.23 g, 0.20 mmol) in THF (8 mL). The reaction mixture was heated to 60 ¡ãC for 10hours, before the reaction was quenched with a saturated aqueous ammonium chloride solution. 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). Washing the resulting solid with smallamount of methanol to give compound 4 (1.99 g, 3.10 mmol, 78percent). 4: orange solid, m.p.139-141 ¡ãC. 1H NMR (300 MHz, CDCl3) delta 1.39 (s, 36H), 4.14 (s, 5H), 4.59 (s, 2H),7.35 (t, J = 1.8 Hz, 1H), 7.62 (d, J = 1.8 Hz, 2H); 13C NMR (75 MHz, CDCl3) delta 31.5 (q),34.9 (s), 67.0 (d), 73.5 (d), 79.7 (s), 88.6 (s), 120.9 (d), 124.4 (d), 135.5 (s), 149.8 (s).Anal. Calcd for C38H49BrFe: C, 71.14; H, 7.70percent. Found: C, 71.30; H, 7.66percent.
The synthetic route of 22385-77-9 has been constantly updated, and we look forward to future research findings.
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