Category: 3975-77-7

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3975-77-7, name is 2-Bromo-1,3,5-tri-tert-butylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-Bromo-1,3,5-tri-tert-butylbenzene

A solution of bromo-2,4,6-tri-tert-butylbenzene (?supermesityl bromide, Mes*Br?, 326mg, 1.00mmol) in pentane (1.5mL) and THF (0.7mL) was cooled to-60C under argon gas cover for the injection of nBuLi (1.13mmol) in hexane (0.50mL). After one hour at rt, the supernatant was withdrawn from the precipitated 2,4,6-tri-tert-butylphenyllithium (Mes*Li), which was then washed with dry pentane (2×1mL). The subsequent addition of anhydrous Et2O (0.6mL) dissolved Mes*Li partially, and the entailing treatment with 2,2,6,6-tetramethylpiperidine (HTMP, 0.034mL, 28mg, 0.2mmol) consumed a corresponding portion of Mes*Li. The mixture was treated with the enone 10 (80mg, 0.30mmol) and kept at-60C for 1h, whereafter Mes*Li had been dissolved entirely. The solution was transferred to an NMR tube (5mm) and observed until 10 (deltaH=6.54ppm) had vanished (24h). The tube should be cooled in ice during the final addition of D2O (0.10mL). The resultant mixture was diluted with aqueous HCl (2M, 2mL) and Et2O (5mL). The acidic aqueous layer was shaken with Et2O (2×5mL) and discarded. The combined Et2O phases were washed with distilled water (3×3mL), dried over Na2SO4, filtered, and concentrated to leave a mixture (108mg) of 19, Mes*H, and partially (81%) deuteriated enone 10 in a 10:68:22M ratio. Analytically pure 19 had mp 202-203C (from 10mL of ethanol). (0032) IR (KBr) nu 3566 (very sharp O-H), 2961, 2870, 1595, 1485, 1474, 1458, 1362, 754cm-1. (0033) 1H NMR (CDCl3, 400MHz) delta 0.94 (s, 9H, 3×Me-1?), 1.04 (d, 4J=1.2Hz, 1H, OH), 1.25 (s, 3H, 5?-Mea), 1.31 (s, 18H, 2×meta-CMe3), 1.35 (s, 3H, 3-Mea), 1.40 (s, 3H, 3-Meb), 1.43 (s, 3H, 1-Mea), 1.49 (s, 3H, 1-Meb), 1.52 (s, 3H, 5?-Meb), 1.90 (d, 2J=15.2Hz, 1H, 4?-Ha), 2.70 (d, 2J=15.2Hz, 1H, 4?-Hb), 5.40 (d, 4J=1.2Hz, 1H, alpha-H), 7.12 (m, 1H, 4-H), 7.14 (m, 1H, 7-H), 7.18 and 7.19 (2m, 2H, 5-/6-H), 7.24 (d, 4J=1.7Hz, 2H, 2×ortho-H), 7.28ppm (t, 4J=1.7Hz, 1H, para-H), assigned through the NOESY correlations 3-Mea+b ? alpha-H ? 4?-Ha ? 4?-Hb ? ortho-H ? meta-C(CH3)3 ? para-H; 1-Mea ? 1-Meb ? HO ? ortho-H; 5?-Mea ? ortho-H ? 5?-Meb ? HO ? 1-Meb ? meta-C(CH3)3; (0034) 13C NMR (CDCl3, 100.6MHz) delta 26.3 (qsept, 1J=125.5Hz, 3J=4.9Hz, 3×Me-1?), 26.7 (qm, 1J=ca. 124 Hz, 5?-Meb), 31.2 (qm, 1J=124.5Hz, 1-Mea), 31.5 (qsept, 1J=125Hz, 3J=4.9Hz, 2×meta-CMe3), 32.30 and 32.32 (2 qm, 1J=126Hz, 1-Meb and 3-Meb), 33.2 (qm, 1J=126Hz, 3-Mea), 35.0 (quat, 2×meta-CMe3), 37.2 (qm, 1J=126.0Hz, 5?-Mea), 37.8 (quat, C-5?), 40.5 (quat, C-2?), 46.3 (quat, C-1), 48.7 (tm, 1J=124Hz, CH2-4?), 49.3 (quat, C-3), 81.3 (quat, C-3?), 120.0 (dt, 1J=153Hz, 3J=6.5Hz, C-para), 120.3 (dt, 1J=152Hz, 3J=6.5Hz, 2×C-ortho), 122.3 (dd, 1J=156Hz, C-7), 122.6 (dd, 1J=156Hz, C-4), 126.3 (dd, 1J=158Hz, 3J=7.4Hz, C-5), 126.8 (dd, 1J=158Hz, 3J=7.4Hz, C-6), 128.6 (dm, 1J=140.6Hz, C-alpha), 147.1 (quat, C-3a), 148.0 (quat, C-7a), 150.6 (sept, 3J=3.7Hz, 2×C-meta), 152.1 (quat, C-ipso), 154.1ppm (quat, C-2), assigned through the coupling constants, comparison with 13b, and the selective {1H} decoupling experiment {CH2 and all CH3} ? C-1 as a d with 3J=8Hz (trans to alpha-H), C-2 as a d with 2J=3.8Hz to alpha-H, C-ipso as a t with 3J=ca. 6 Hz, C-meta as a. Anal. calcd for C37H56O (516.9): C, 85.98; H, 10.92. Found: C, 85.93; H, 10.83.

The synthetic route of 3975-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Knorr, Rudolf; Schmidt, Barbara; Freudenreich, Johannes; von Roman, Therese; Tetrahedron; vol. 74; 52; (2018); p. 7466 – 7471;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 3975-77-7, name is 2-Bromo-1,3,5-tri-tert-butylbenzene, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 3975-77-7, Recommanded Product: 3975-77-7

2,4,6-Tri-tert-butylbenzoicacid (mes*CO2H, S3). The Br/Liinterchange reaction between mes*Br and n-BuLi in Et2O (see above)was carried out according to the protocol of Staab and LauerS9 but with a reaction period shortened to lessthan 1 hour at room temperature. Afterpouring onto solid CO2 andaqueous workup, the acid fraction furnished mes*CO2H (S3, crude yield up to 75%); m.p.284-286 C (toluene), Ref. S9: 298-300 C.1H NMR (80 MHz, 2,4,6-Tri-tert-butylbenzoicacid (mes*CO2H, S3). The Br/Liinterchange reaction between mes*Br and n-BuLi in Et2O (see above)was carried out according to the protocol of Staab and LauerS9 but with a reaction period shortened to lessthan 1 hour at room temperature. Afterpouring onto solid CO2 andaqueous workup, the acid fraction furnished mes*CO2H (S3, crude yield up to 75%); m.p.284-286 C (toluene), Ref. S9: 298-300 C.1H NMR (80 MHz,

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, 2-Bromo-1,3,5-tri-tert-butylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Knorr, Rudolf; Rossmann, Eva C.; Knittl, Monika; Boehrer, Petra; Tetrahedron; vol. 70; 34; (2014); p. 5332 – 5338;,
Bromide – Wikipedia,
bromide – Wiktionary

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 3975-77-7 as follows. Recommanded Product: 3975-77-7

General. 1H NMR studies revealed that?supermesityl bromide? (mes*Br, S1)S7 and n-BuLi coexist in t-BuOMeover more than 18 h at room temperature, while this solvent is very slowlydeprotonated by n-BuLi with formation of isobutene. Similarly, t-BuLideprotonates t-BuOMe, leaving S1intact.When prepared from S1 withn-BuLi, mes*Li (S2)is not stable in a THF solution at ambient temperature. However, its stabilityis greatly enhanced on dilution of the THF with pentane. Moreover, a portion ofS2 will crystallize from pentane/THF(4:1)S8 and may be washedwith dry petroleum ether if pure mes*Li is required.In Et2O atroom temperature, the formation of mes*Li(S2) from S1and n-BuLiwas complete within 10 min; therefore,the traditional long reaction periods of this Br/Li interchange reaction in thesolvent Et2O can be considerably shortened, and the presence of apromoter (such as TMEDA) is unnecessary.This Et2O solution containing S2 and 1-bromobutane was stable for several hours at ambienttemperature and for at least 18 hours under argon gas in a refrigerator. Although S2in Et2O was protonated very slowly by N,N-diisopropylamine atroom temperature, proton transfer fromcyclohexylamine (pKa =41.6) to S2 was fast andquantitative. Procedure. A dry NMR tube (5 mm) was charged with mes*BrS7 (S1,80 mg, 0.24 mmol), pentane (0.40 mL), and anhydrous THF (0.10 mL), then cooled to -70 C during the addition of n-BuLi (0.37 mmol) in hexanes (0.14 mL)and for further 60 min. The colorless precipitate of S2 was washed with pentane (2 ) and then dissolved in anhydrous Et2O(0.50 mL), showing dH = 7.01 ppm for 3-/5-H of S2. The addition of cyclohexylamine (0.027 mL, 0.24 mmol) at -70 C converted S2 completely into 1,3,5-tri-tert-butylbenzene(dH = 7.31 ppm), which was isolated afterquenching with solid CO2 andaqueous workup (no acid S3) as apure, colorless powder (35 mg, 58%). This indicates that pKa> 41.6 for S2. A similar run with N,N-diisopropylamine(ca. 2 equiv, pKa = 34.4)in place of cyclohexylamine disclosed a very slow proton transfer at room temperature (ca. 30% in 10 min).

According to the analysis of related databases, 3975-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Knorr, Rudolf; Rossmann, Eva C.; Knittl, Monika; Boehrer, Petra; Tetrahedron; vol. 70; 34; (2014); p. 5332 – 5338;,
Bromide – Wikipedia,
bromide – Wiktionary