Month: February 2021

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. 58534-95-5, name is 3-Bromo-2-fluoroaniline, A new synthetic method of this compound is introduced below., Quality Control of 3-Bromo-2-fluoroaniline

To a solution of 3-bromo-2-fluoroaniline (20.0 g, 105 mmol) in HC1 (12.0 M, 100 mL, 11.4 eq) was added a solution of NaN02 (10.9 g, 158 mmol, 1.50 eq) in water (20.0 mL) drop-wise at 0 C. The mixture was stirred at 0 C for 1 h. SnCl2.2H20 (71.3 g, 316 mmol, 3.00 eq) in H20 (40.0 mL) was added to the mixture at 0C. The mixture was stirred for 12 h at 20 C. The reaction mixture was filtered. The filter cake was washed with EtOAc (20.0 mL) and triturated with EtOAc (30.0 mL). The filter cake was dried to afford (3-bromo-2-fluorophenyl)hydrazine hydrochloride. LC-MS: mz 205.1 [M+H]+

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:
Patent; LAMA, Lodoe; TUSCHL, Thomas; TOMITA, Daisuke; PATEL, Dinshaw; GLICKMAN, J. Fraser; KAMEI, Taku; MILLER, Michael; ASANO, Yasutomi; OKAMOTO, Rei; HASHIZUME, Shogo; AIDA, Jumpei; IMAEDA, Toshihiro; MICHINO, Mayako; KUROITA, Takanobu; (107 pag.)WO2019/153002; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1154740-48-3, A common heterocyclic compound, 1154740-48-3, name is 6-Bromo-5-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine, molecular formula is C9H10BrNO, 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.

b) 6-Bromo-4-(5-difluoromethyl-6-methoxy-pyridin-3-yl)-5-methyl-3,4-dihydro-2H-benzo[1,4]oxazine A solution of 6-bromo-5-methyl-3,4-dihydro-2H-benzo[1,4]oxazine (500 mg, 2.19 mmol), Intermediate IA6 (574 mg, 2.41 mmol), NaOtBu (421 mg, 4.38 mmol), BrettPhos (CAS registry 1070663-78-3) (59 mg, 0.11 mmol) and [BrettPhos]palladacycle (CAS registry 1148148-01-9) (88 mg, 0.11 mmol) in dioxane (11 ml) was stirred at 100 C. for 18 h. Catalyst and ligand were reloaded and stirring was continued at 100 C. for 48 h. The reaction mixture was cooled down to rt, diluted with EtOAc and washed with sat. aq. NaHCO3 soln. The organic layer was dried over MgSO4, concentrated to afford a brown oil. Purification by flash chromatography on silica gel (cyclohexane/EtOAc 100:0 to 80:20) afforded the title compound as a brown oil (150 mg, 18% yield). HPLC RtM1=1.34 min; ESIMS: 385, 387 [(M+H)+].

The synthetic route of 1154740-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CARAVATTI, Giorgio; CHAMOIN, Sylvie; FURET, Pascal; HOGENAUER, Klemens; HURTH, Konstanze; KALIS, Christoph; KAMMERTOENS, Karen; LEWIS, Ian; MOEBITZ, Henrik; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; WOLF, Romain; ZECRI, Frederic; US2013/165436; (2013); 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. 615-36-1, name is 2-Bromoaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 615-36-1

General procedure: The 25 mL RB flask was charged with arylboronic acid (1 mmol), N-nucleophile (2 mmol), Ni(OAc)2*4H2O/1a (10 mol % of Ni(II) salt and 20 mol % of 1a), TMG (2 mmol), and toluene (1 ml). The reaction mixture was stirred at 60 C for 24 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL), and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using hexane to afford the Chan-Lam product in high purity.

The synthetic route of 615-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Keesara, Srinivas; Tetrahedron Letters; vol. 56; 48; (2015); p. 6685 – 6688;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 45762-41-2, 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. 45762-41-2, name is 4-Bromo-2-ethylaniline, This compound has unique chemical properties. The synthetic route is as follows.

4-Bromo-2-ethyl-aniline (2ml_, 14 mmol) dissolved in anhydrous pyridine (35 ml) at toom temperature was treated with methylsulfonyl chloride (1.3 ml_, 16.8 mmol). The reaction was stirred at that temperature for 15 hours before it was diluted with EtOAc. The mixture was washed with H2O, brine and dried over MgSO4. The solvent was removed in vacua and the residue was purified with flash chromatography (SiO2, 5-30% EtOAc in hexanes) to afford thedesired product (3.1 g, 81% yield). 1H NMR (300 MHz, CDCI3): 6 1.25 (t, J=7.5 Hz, 3 H), 2.61-2.68 (m, 2 H), 3.02 (s, 3 H), 6.36 (s, 1 H), 7.36-7.39 (m, 3 H).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-ethylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; PFIZER INC.; WO2006/18725; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 630-17-1, name is 1-Bromo-2,2-dimethylpropane, 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 630-17-1, name: 1-Bromo-2,2-dimethylpropane

General procedure: In the presence of tetrabutylammoniumiodide (738 mg, 2.0 mmol), 12 (800 mg,3.71 mmol) was alkylated with neopentyl bromide (2.4 mL,19 mmol) at 50 C in DMF to give 1-O-benzyl-2-O-neopentyl-3,4-O-isopropylidene-D-erythritol (14g, 409 mg, 40%) as colorless oil,[a]D23 +15.0 (c 1.05, CHCl3). IR (neat): 1477, 1454, 1369, 1253,1215, 1084, 1061, 1030 cm1. 1H NMR (500 MHz, CDCl3) d: 0.90[9H, s, OCH2C(CH3)3], 1.35/1.41 [each 3H, s, C(CH3)2], 3.13/3.35[each 1H, d, J = 8.3, OCH2C(CH3)3], 3.46 (1H, ddd, J = 6.3, 4.9, 3.2,H-2), 3.55 (1H, dd, J = 10.6, 4.9, H-1a), 3.68 (1H, dd, J = 10.6, 3.2,H-1b), 3.95 (1H, dd, J = 8.3, 6.3, H-4a), 4.05 (1H, dd, J = 8.3, 6.3, H-4b), 4.16 (1H, ddd, J = 6.3, 6.3, 6.3, H-3), 4.56 (2H, s, OCH2Ph),7.25-7.36 (5H, m, arom.). 13C NMR (125 MHz, CDCl3) d: 25.4/26.7[C(CH3)2], 26.7 [OCH2C(CH3)3], 32.2 [OCH2C(CH3)3], 66.7 (C-4),70.0 (C-1), 73.4 (OCH2Ph), 75.6 (C-3), 79.9 (C-2), 81.5 [OCH2C(CH3)3], 108.9 [C(CH3)2], 127.5/128.3 (d, arom.), 138.4 (s, arom.).LRMS (FAB, pos.) m/z: 345 [M+Na]+. HRMS (FAB, pos.): calcd forC19H30O4Na 345.2042, found 345.2052.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,2-dimethylpropane, and friends who are interested can also refer to it.

Reference:
Article; Tanabe, Genzoh; Xie, Weijia; Balakishan, Gorre; Amer, Mumen F.A.; Tsutsui, Nozomi; Takemura, Haruka; Nakamura, Shinya; Akaki, Junji; Ninomiya, Kiyofumi; Morikawa, Toshio; Nakanishi, Isao; Muraoka, Osamu; Bioorganic and Medicinal Chemistry; vol. 24; 16; (2016); p. 3705 – 3715;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 3638-73-1, These common heterocyclic compound, 3638-73-1, name is 2,5-Dibromoaniline, 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.

General procedure: 1-Hydroxynaphthalene-2-carboxylic acid (5.3 mmol) and the corresponding substituted aniline (5.3 mmol) were suspended in 30 mL of dry chlorobenzene. Phosphorous trichloride (2.65 mmol) was added dropwise, and the reacting mixture was heated in the microwave reactor at maximal allowed power 500 W and 130 C, using infrared flask-surface control of temperature, for 15 min. The solvent was evaporated under reduced pressure, the solid residue washed with 2 M HCl, and the crude product was recrystallized from aqueous ethanol. All the studied compounds are presented in Table 1.

The synthetic route of 3638-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gonec, Tomas; Kos, Jiri; Pesko, Matus; Dohanosova, Jana; Oravec, Michal; Liptaj, Tibor; Kralova, Katarina; Jampilek, Josef; Molecules; vol. 22; 10; (2017);,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 4101-68-2, 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. 4101-68-2, name is 1,10-Dibromodecan belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1,10-Bisazidodecane NaN3 (1.30 g, 20.0 mmol) was suspended in a solution of 1,10-dibromodecane (2.42 g, 10.0 mmol) in dry dimethylformamide (15 mL). After stirring for 12 h at 60 C. water (15 mL) was added and the mixture was extracted with diethyl ether (3*100 mL). The organic layer was washed with water (3*50 mL), dried over Na2SO4 and evaporated. The crude product was purified by chromatography on silica gel (0%?20% ethyl acetate in cyclohexane). Yield: 6.82 mmol, 68% yellowish oil. 1H: [300 MHz, CDCl3] delta=1.30-1.54 (m, 12H), 1.51-1.68 (m, 4H), 3.26-3.35 (m, 4H) ppm. HRMS: [C10H20N6] m/z cal. [M+H]+=225.1822 m/z found [M+H]+=225.1821.

The synthetic route of 1,10-Dibromodecan has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arenz, Christoph; Davies, Brian Patrick; Neubacher, Saskia; Klemm, Claudine Mercedes; US2009/92980; (2009); A1;,
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 1435-52-5 as follows. name: 1,4-Dibromo-2-fluorobenzene

To a stirred solution of 1,4-dibromo-2-fluorobenzene (100 g, 395.2 mmol) in ethylene glycol(510 mL), NMP (50 mL) was added at rt under N2 atmosphere. Then tBuOK (155.2 g,1383.0 mmol) was added slowly over 10 mm at 10 C. The reaction mixture was heated at100 C for 12 h. The completion of the reaction was monitored by TLC. The reaction mixture was cooled to rt and diluted with water (200 mL) and stirred for 15 mm at rt. The resulting solid was filtered and washed with ethylene glycol (2 x 30 mL). Water (2200 mL) was added to the filtrate, the solution was cooled to 15 C and stirred for I h. The resulting precipitate was filtered and washed with water (2 x 100 mL), pet ether (2 x 100 mL) and dried. It was further dried with the addition of toluene and its evalportaion (3 x 200 mL). It was then use in the next step without further purification. Yield: 77.5% (90 g, pale brown solid). 1H NMR (400 MHz, CDCI3): 6 7.41 (d, J = 8.4 Hz, I H), 7.06 (d, J = 2.0 Hz, I H), 7.02 (dd, J = 8.4, 2.4 Hz, IH), 4.14 (t, J = 4.4 Hz, 2H), 4.03-4.00 (m, 2H), 2.36 (t, J = 6.4 Hz,IH).

According to the analysis of related databases, 1435-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh, S.; GIRI, Awadut, Gajendra; (280 pag.)WO2017/144633; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, 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 138526-69-9, Safety of 1-Bromo-3,4,5-trifluorobenzene

At room temperature, dry diethyl malonate (1140.2 g, 7.12 mol) is initially charged in a 1.6 l apparatus with anchor stirrer, and sodium ethoxide (244.5 g, 3.59 mol) is added as a solid. Owing to the energy of reaction released, the internal temperature increases to about 60 C. After the reaction has ended, the ethanol formed is distilled off under reduced pressure (400 mbar) and simultaneous increase of the temperature from 60 to 80 C. At 80 C., the pressure is gradually reduced to 10 mbar. At atmospheric pressure, the residue is then cooled to 75 C., and CuBr (53.4 g, 0.37 mol) and 3,4,5-trifluorobromobenzene (338.4 g, 1.60 mol) are then added successively over a period of 20 minutes, and the mixture is kept at 75 C. for another 18 hours. After the reaction has ended, the reaction mixture is cooled to 15 C. and, with stirring, added to a mixture, cooled to 10 C., of hydrochloric acid (36% strength, 260.9 g) and water (512.8 g). The reaction mixture obtained is filtered. Following separation of the phases of the filtrate, water (512.8 g) is added to the organic phase, and the pH is adjusted to 3.8 by addition of potassium carbonate (5.9 g, 50% strength solution in water). The phases are separated again, and the organic phase is then freed from volatile components under reduced pressure (0.5 mbar) up to an internal temperature of 127 C. According to quantitative 19F-NMR spectroscopy, 79.6% of the residue (478.4 g) consisted of diethyl 3,4,5-trifluorophenylmalonate. This corresponds to a diethyl 3,4,5-trifluorophenyl-malonate yield of 82.0%.

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, 1-Bromo-3,4,5-trifluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF SE; US2010/56820; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 49764-63-8, These common heterocyclic compound, 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, 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.

General procedure: Triphenylstibane(35.5 mg, 0.1 mmol, 10 mol%) and diamine 2 (1.2 mmol) were added to a solution of -hydroxy ketone 1(1 mmol) in toluene (6 mL) under air. The solution was stirred at room temperature and monitored byTLC. The reaction mixture was concentrated under reduced pressure and the residue was purified bycolumn chromatography (CH2Cl2) on silica gel. The products were confirmed by comparison of mp,NMR data, and MS spectra with that in the literature. 822:

The synthetic route of 49764-63-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Matsumura, Mio; Takada, Rie; Ukai, Yuu; Yamada, Mizuki; Murata, Yuki; Kakusawa, Naoki; Yasuike, Shuji; Heterocycles; vol. 93; 1; (2016); p. 75 – 83;,
Bromide – Wikipedia,
bromide – Wiktionary