Tag: M.W=200-300

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,
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Synthetic Route of 22034-13-5, 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 22034-13-5 as follows.

A mixture of (9,9-di-n-hexyl-9H-fluoren-2-yl)boronic acid [J. Am. Chem. Soc, 2004, 126, 13695-13702] (915 mg, 2.42 mmol), 4-bromobenzo[c] [l,2,5]thiadiazole [J. Phys. Chem. B, 2012, 116, 7259-7268] (434 mg, 2.02 mmol), and potassium carbonate (1.20 g, 8.70 mmol) in toluene (20 mL), ethanol (8 mL), and water (12 mL) was placed under vacuum until boiling and backfilled with argon six times. Tetrakis(triphenylphosphine)- palladium(O) (100 mg, 0.087 mmol) was added and the solution heated in an oil bath held at 100¡ãC overnight under a blanket of argon. The solution when then cooled, diluted with water (90 mL), diethyl ether (90 mL), brine (60 mL), and the layers separated. The aqueous solution was extracted with diethyl ether (3 x 60 mL) and the combined organic extracts were washed with water (2 x 60 mL), brine (60 mL), dried over anhydrous magnesium sulphate, filtered on a silica plug, and the solvent removed in vacuo. The crude residue was purified by column chromatography over silica using a dichloromethane: light petroleum mixture (0: 1 to 1 : 10) as eluent to afford AL03-77 as yellow/green oil after removal of the solvent (751 mg, 79percent). 1H NMR (500 MHz, CDC13) delta: 0.66-0.83 (10H, m, HexH), 1.00- 1.12 (12H, m, HexH), 1.95-2.09 (4H, m, HexH), 7.31- 7.40 (3H, m, FIH), 7.71 (1H, dd, = 8.5, 8.5 Hz, BTH), 7.76 (2H, dd, = 1.0, 7.0 Hz, FIH), 7.85 (1H, dd, = 0.5, 8.0 Hz, BTH), .90 (1H, d, = 0.5 Hz, BTH), 7.97 (1H, dd, = 1.5, 8.0 Hz, FIH), 8.00 (1H, dd, = 1.0, 8.5 Hz, FIH). HRMS (ESI-MS) for C31H36N2S [M + Na]+ Calcd: 491.2491 (100percent), 492.2522 (34percent), 493.2511 (10percent). Found: 491.2491 (100percent), 492.2500 (40percent), 493.2480 (12percent).

According to the analysis of related databases, 22034-13-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF QUEENSLAND; BURN, Paul Leslie; SHAW, Paul Edward; (64 pag.)WO2019/79860; (2019); A1;,
Bromide – Wikipedia,
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Reference of 1435-51-4, These common heterocyclic compound, 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, 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 mixture of Pd(OAc)2 (88 mg, 0.394 mmol) and BINAP (294 mg, 0.473 mmol) in dioxane (8 mL) was stirred in a sealed tube for ~5 min. To the mixture was then added 1 ,3- dibromo-5-fluorobenzene (0.496 mL, 3.94 mmol) and (tetrahydro-2H-pyran-4- yl)methanamine hydrochloride (299 mg, 1 .969 mmol), stirring was continued for additional ~5 min and KOtBu (486 mg, 4.33 mmol) was added. The resulting mixture was heated at 93 C for ~18 hrs. The reaction mixture was cooled to room temperature, diluted with EtOAc (~50 mL) and MeOH (~10 mL), filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, 40 g, EtOAc/heptane = 5/95 to 30/70] providing 3-bromo-5-fluoro-N-((tetrahydro-2H-pyran-4-yl)methyl)aniline (220 mg) as a colorless liquid. LCMS (m/z): 289.9 [M+H]+; Rt = 1 .03 min.

The synthetic route of 1435-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul, A.; HU, Cheng; JIN, Xianming; NG, Simon, C.; PFISTER, Keith, B.; SENDZIK, Martin; SUTTON, James; WO2012/101064; (2012); A1;,
Bromide – Wikipedia,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H5BrF3N

A. 2-Acetamido-5-bromobenzotrifluoride A solution of 2-amino-5-bromobenzotrifluoride (1.623 g, 6.76 mmol, Aldrich) in acetic anhydride (10 mL) was stirred at room temperature for 12 h to produce a white needle precipitate. It was filtered to give 1.840 g (99.7%) of title compound. Mp: 140-2 C., 1 H-NMR (CDCl3): delta2.212 (s, 3H); 7.358(s, 1H); 7.659(d, 1H, J=8.7 Hz); 7.726(d, 1H, J=1.8 Hz); 8.118 (d, 1H, J=8.4 Hz).

The synthetic route of 445-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The State of Oregon, acting by and through The Oregon State Board of Higher Education, acting for and on behalf of The Oregon Health Sciences University; The University of Oregon; The Regents of the University of California; US5514680; (1996); A;,
Bromide – Wikipedia,
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Synthetic Route of 103273-01-4, 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. 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Synthesis of 2-(tert-butyl)-6-aminophenanthridine 35.7 g (190 mmol) 2-(1,3,2-dioxaborinan-2-yl)benzonitrile, 31.9 g (158 mmol) 2-bromo-4-(tertbutyl)aniline, 3.6 g (3.16 mmol) tetrakis(triphenylphosphine) palladium(0) and 59.0 g (427 mmol) K2CO3 were heated to reflux in a 2 L flask containing 400 ml toluene and 300 mL ethanol. The reaction mixture was heated for 19 hours under constant N2 purge. HPLC of the reaction mixture indicated consumption of the starting aniline. The mixture was cooled and then filtered to remove the base. The base was washed with EtOAc to remove trace organic. The combined filtrate was evaporated down to give impure oil. The oil was purified on a column of silica using 95/5/0.05 CH2Cl2/MeOH/NH4OH as eluent to obtain separation. The product fractions were evaporated of solvent and the resultant residue recrystallized from CH2Cl2/hexanes to yield 14.0 g of the target compound as white solids (35.5% yield, confirmed by GC-MS).

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-4-(tert-butyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Universal Display Corporation; Knowles, David; Lin, Chun; Mackenzie, Peter; Tsai, Jui-Yi; Walters, Robert W.; Beers, Scott; Brown, Cory S.; Yeager, Walter; (85 pag.)US9281483; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, This compound has unique chemical properties. The synthetic route is as follows., name: 1-(4-Bromophenyl)ethylamine

General procedure: To a stirred solution of ortho-benzoquinone (0.825 mmol, 1.0equiv) in acetonitrile (4.0 mL), was added dropwise a solution ofprimary amine (0.825 mmol, 1.0 equiv) in acetonitrile (4.25 mL)over 5 min under an argon atmosphere. The deep green colouredsolution was stirred at room temperature for 2e8 h. Aftercompletion of the reaction, as indicated by TLC, the reactionmixture was cooled to 0C. To this, triethylamine (0.34 mL,2.48 mmol, 3 equiv) and iodine granules (0.419 g, 1.65 mmol, 2 eq),were added. The resulting mixture was stirred vigorously for10e60 min under argon atmosphere. Upon completion, the reac-tion mixture was diluted with water and extracted with EtOAc(3 5 mL). The combined organic layer was washed with aqueoussaturated sodium thiosulfate (1 10 mL) and brine (2 10 mL),respectively, dried over Na2SO4, ltered, and concentrated in vacuo.The crude residue was puried by silica gel column chromatog-raphy eluting with pentane:EtOAc (95:5e80:20 v:v) to afford thedesired benzo[1,4]oxazine product.

According to the analysis of related databases, 24358-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Vasu, Dhananjayan; Leitch, Jamie A.; Dixon, Darren J.; Tetrahedron; vol. 75; 50; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 5003-71-4,Some common heterocyclic compound, 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, molecular formula is C3H9Br2N, 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.

Prepared from 3-bromopropylamine hydrobromide and BOC2O in the presence of base in dichloromethane, 9.89 mmol: 1H NMR (CDCl3) delta 5.07 (br, 1H), 3.31 (t, 2H, J=6.6 Hz), 3.12 (apparent br q, 2H, J=6.0 Hz), 1.92 (p, 2H, J=6.6 Hz), 1.30 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromopropan-1-amine hydrobromide, its application will become more common.

Reference:
Patent; Synaptic Pharmaceutical Corporation; US6727264; (2004); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 845866-81-1,Some common heterocyclic compound, 845866-81-1, name is 2-Bromo-1-(difluoromethyl)-4-fluorobenzene, molecular formula is C7H4BrF3, 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.

The 2-difluoromethyl-5-fluorobenzaldehyde used as starting material was prepared as follows :-; Isopropylmagnesium chloride – lithium chloride complex (IM, 21.46 mL, 21.46 mmol) was added to 2-bromo-l-(difluoromethyl)-4-fluorobenzene (4.39 g, 19.51 mmol) in THF (120 mL) cooled to -200C under nitrogen. The resulting solution was stirred at -200C for 1 hour. N,N-Dimethylformamide (1.813 mL, 23.41 mmol) was added, and the mixture stirred for a further 1 hour, maintaining the temperature in the range -15 to -200C. The mixture was allowed to warm to ambient temperature, then 2M hydrochloric acid (100 mL) was added and the mixture was extracted with EtOAc (150 mL). The organic layer was washed with saturated sodium bicarbonate (120 mL) and concentrated to yield crude product. The crude product was purified by flash silica chromatography, elution gradient 5 to 10% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 2- (difluoromethyl)-5-fluorobenzaldehyde (1.250 g, 36.8%) as a colourless liquid. IH NMR (399.9 MHz, CDC13) delta 7.26 (IH, t), 7.37 – 7.43 (IH, m), 7.63 – 7.67 (IH, m), 7.78 – 7.82 (IH, m), 10.19 (IH, d); m/z = 173 [M-H]-.

The synthetic route of 845866-81-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BRADBURY, Robert, Hugh; CARR, Gregory, Richard; RABOW, Alfred, Arthur; RAO KORUPOJU, Srinivasa; TUMMA, Harikrishna; WO2010/92371; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 69321-60-4, 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. 69321-60-4 name is 2,6-Dibromotoluene, 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.

According to scheme 2, step viii: To a mixture of intermediate 15b (2 g, 5.68 mmol,1 eq) and 1,3-dibromo-2-methylbenzene (1.42 g, 5.68 mmol, 72.57 uL, 1 eq) in dioxane (30 mL) and H2O (2 mL) were added Pd(dppf)Cl2 (207.76 mg, 283.93 umol, 0.05 eq) and Na2CO3 (1.81 g, 17.04 mmol, 3 eq) in one portion at 25C under N2. The mixture was stirred at 90C for 12 hours. The residue was poured into ice-water (w/w = 1/1) (50 mL). The aqueous phase was extracted with ethyl acetate (50 mL x 3). The combined organic phase was washed with brine (50 mL), dried with anhydrous Na2SO4, filtered and concentrated in vacuo to afford Intermediate 53 (1.4 g, 3.54 mmol, 62.37% yield) as a yellow solid. 1H NMR (CDCl3, 400 MHz) delta 8.92 (d, J = 4.8 Hz, 2H), 7.75 (s, 1 H), 7.54 (d, J = 7.6 Hz, 1 H), 7.40 (t, J = 4.8 Hz, 1 H), 7.11-7.06 (m, 2H), 6.24 (s, 1 H), 3.00 (t, J = 9.6 Hz, 2H), 2.64 (t, J = 9.6 Hz, 2H), 2.42 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dibromotoluene, and friends who are interested can also refer to it.

Reference:
Patent; Pragma Therapeutics; DUVEY, Guillaume; CELANIRE, Sylvain; (118 pag.)EP3459939; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 51554-93-9, name is 1-Bromo-4-octylbenzene, A new synthetic method of this compound is introduced below., name: 1-Bromo-4-octylbenzene

General procedure: A 3-neck round-bottomed flask equipped with a thermometer and a condenser was flame-dried and flushed with Ar. The flask was then charged with Mg0 (1.1 eq.), a single I2 crystal and another vacuum/Ar cycle was performed. Et2O (C=0.65M) was added resulting in a bright orange suspension of Mg0 pellets. Phenyl octyl bromide (1.0 eq.) was then added in one portion and the suspension was heated via a heatgun until the internal temperature reached 32C and stabilized for 5-10s, indicating that the Grignard formation had started. The reaction was stirred at rt until disappearance of the starting material by 1H NMR analysis (e.g.?1h). (0031) The Grignard solution (3.0 eq., C=0.65M) was then syringed to another flask containing substrate (1.0. eq.) in dry Et2O (C=0.05M). The solution was stirred at rt until disappearance of the starting material by TLC analysis. Saturated aqueous NH4Cl solution was added and the aqueous layer was extracted x2 with EtOAc. The organic layers were collected, washed x1 brine, dried over Na2SO4, filtered, concentrated in vacuo.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Garsi, Jean-Baptiste; Sernissi, Lorenzo; Vece, Vito; Hanessian, Stephen; McCracken, Alison N.; Simitian, Grigor; Edinger, Aimee L.; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 217 – 242;,
Bromide – Wikipedia,
bromide – Wiktionary