Tag: M.W=100-200

These common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, 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. Quality Control of 3-Bromo-4-methylaniline

Intermediate 28A: 5-Bromo-2-iodo-4-methylaniline A solution of 3-bromo-4-methylaniline (5.00 g, 26.9 mmol), N-iodosuccinimide (4.53 g, 20.2 mmol) and bis(pyridine)iodonium tetrafluoroborate (2.70 g, 7.26 mmol) in DCM (100 mL) was stirred at room temperature overnight. The mixture was diluted with DCM, washed sequentially with saturated aqueous NaHSO3 and water, and dried and concentrated. The residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes (sequentially 1%, 2% and 3%), to provide 5-bromo-2-iodo-4-methylaniline as a yellow solid (5.27 g, 63% yield). Mass spectrum m/z 312, 314 (M+H)+. 1H NMR (500 MHz, CDCl3) delta 7.49 (d, J=0.6 Hz, 1H), 6.94 (s, 1H), 4.17-3.91 (br.s, 2H), and 2.25 (s, 3H).

The synthetic route of 3-Bromo-4-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Batt, Douglas G.; Bertrand, Myra Beaudoin; Delucca, George; Galella, Michael A.; Ko, Soo Sung; Langevine, Charles M.; Liu, Qingjie; Shi, Qing; Srivastava, Anurag S.; Tino, Joseph A.; Watterson, Scott Hunter; US2014/378475; (2014); A1;,
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Synthetic Route of 452-74-4, 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. 452-74-4 name is 1-Bromo-2-fluoro-4-methylbenzene, 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.

To a stirred solution of 4-bromo-3-fluorotoluene (10 g, 52.9 mmol) in H2SO4 (100 mL) was added [KN03] (5.34 g, 52.9 mmol) at [0C.] After stirring overnight at room temperature, the reaction mixture was poured into ice (200 g) and extracted with EtOAc (3 x 300 mL). The organic solution was washed with brine (200 mL), dried (Na2SO4), and concentrated to give 12.35 g (100%) of title compound as a pale yellow [OIL.’H NMR (CDCIS)] : [300 MHZ No. 8. ]29 (d, [J= 6.] 30 Hz, 1H), 7.12 (d, J= 8.61 Hz, 1H), 2.60 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-fluoro-4-methylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; WYETH; VIROPHARMA INCORPORATED; WO2003/99824; (2003); A1;,
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Synthetic Route of 1003-98-1,Some common heterocyclic compound, 1003-98-1, name is 2-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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.

30.0 g (0.172 mol) 4-chloro-3-fluoro-phenylboronic acid and 29.7 g (0.156 mol) 2-bromo-4-fluoroaniline, in an oxygen-free atmosphere, are suspended in a mixture of 170 ml toluene, 17 ml ethanol and 160 ml of saturated sodium carbonate solution in an argon atmosphere. 3.6 g tetrakis(triphenylphosphine) palladium (0) is added to the reaction mixture, and it is stirred for 12 hours at 80 C. The organic phase is separated and the aqueous phase is extracted with acetic acid ethyl ester. The combined organic phases are concentrated, and the residue is chromatographed with cyclohexane/acetic acid ethyl ester (3:1) on silica gel.The reaction yields 26.1 g (69.7% of the theoretical yield) of 4′-chloro-3′,5-difluorobiphenyl-2-amine [log P (pH 2.3)=3.18].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; Bayer Cropscience AG; US2008/242708; (2008); A1;,
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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. 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 51376-06-8

5-bromo-2,1,3-benzoxadiazol (2.74 g) (which can be prepared according to Org. Proc. Res. Dev., (2003), 7, 436-445), cesium carbonate (5.38 g), 2,2′- bis(diphenylphosphino)-1,1′-binapthyl (0.68 g) and tris-(dibenzylideneacetone) dipalladium(O) (0.5 g) were added to a solution of (5S)-3-[3-fluoro-4-(piperidin-4- yloxy)phenyl]-5-[(isoxazol-3-ylamino)methyl]-1,3-oxazolidin-2-one (5 g) (obtained from Step b) in dry dimethylformamide (15 mL) and the reaction mixture was heated at 100 C for about 17 hours. The reaction mixture was filtered and the solvent was evaporated. The crude product thus obtained was purified by column chromatography using 1 % methanol in dichloromethane to yield the title product (0.4g). Melting point: 134-140 C; EIMS (m/z): 495.25;1HNMR(DMSO): delta 8.41 (s, 1H), 7.88 (d, 1H), (d, 1H), 7.6 (dd, 1H), 7.32 (t, 1H), 7.25 (d, 1H), 6.88 (s, 1H), 6.56 (t, 1H), 6.03 (s, 1H), 4.8 (m, 1H), 4.63-4.62 (m, 1H), 4.17 (t, 1H), 3.81 (m, 4H), 3.49-3.43 (m, 3H), 2.07 (m, 2H), 1.8 (m, 2H).

The synthetic route of 51376-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/35283; (2006); A1;,
Bromide – Wikipedia,
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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. 2695-48-9, name is 8-Bromo-1-octene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H15Br

(9RS,12S)-Isomer A Grignard reagent was prepared from 1-bromo-7-octene (6.80 g, 36 mmol) and Mg (1.08 g, 45 mmol) in dry THF (30 mL) in the presence of a small amount (20 mg) of I2 under argon. A solution of (S)-7 (5.77 g, 26 mmol) in dry THF (10 mL) was added dropwise to the ice-cooled and stirred Grignard reagent at 0-10 C. Stirring was continued for 1 h at 0-5 C, and the mixture was left to stand overnight at room temperature. It was then poured into ice and dil HCl, and extracted with Et2O. The Et2O solution was washed successively with water, NaHCO3 solution, and brine, dried (MgSO4), and concentrated in vacuo. The residue (10.9 g) was chromatographed over SiO2 (70 g). Elution with hexane gave 1.0 g of hydrocarbons, and further elution with hexane/EtOAc (20:1) afforded 6.42 g (74%) of (9RS,12S)-8 as a colorless oil, nD25=1.4638; [alpha]D25 +0.16 (c 2.58, hexane); numax (film): 3348 (br m), 3077 (m), 2926 (s), 1641 (m), 1463 (m), 992 (m), 909 (s); deltaH (CDCl3): 0.860 (1.5H, d, J 6.4), 0.865 (1.5H, d, J 6.4), 1.05-1.20 (2H, m), 1.20-1.50 (28H, br m), 2.04 (4H, q-like, J 6.4), 3.55 (1H), 4.925 (2H, d-like, J 10.4), 4.980 (2H, d-like, J 17.2), 5.75-5.88 (2H, m); GC-MS (same conditions as those for 3): tR 23.60 (90.6%, 8), 27.15 min (6.8%, M+=360), MS of (9RS,12S)-8 (EI, 70 eV): m/z: 334 (<1) [M+-2], 318 (4) [(M-H2O)+], 207 (4), 165 (5), 149 (6), 137 (11), 123 (32), 109 (42), 94 (66), 81 (86), 69 (69), 67 (53), 55 (100), 41 (40). HRMS calcd for C23H44O: 336.3392, found: 336.3388. The synthetic route of 2695-48-9 has been constantly updated, and we look forward to future research findings. Reference:
Article; Mori, Kenji; Akasaka, Kazuaki; Matsunaga, Shigeki; Tetrahedron; vol. 70; 2; (2014); p. 392 – 401;,
Bromide – Wikipedia,
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Reference of 7745-91-7, These common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, 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.

[0240] To a cooled solution of 3-bromo-4-methylaniline (20 g, 107.5 mmol) in nitrobenzene (11.1 rriL, 107.5 mmol) and glycerol (19.6 mL, 268.8 mmol) at 0 C was added cone. H2SO4 (48 mL, 2.4 vol per g) slowly over a period of 24 min. The reaction temperature was gradually increased to 150 C, and the reaction mixture was stirred at 150 C for 6 hrs. Then it was allowed to cool down to r.t, poured into crushed ice, and extracted with Ethyl Acetate (3 x 500 mL). Combined organic layers were washed with water (300 mL), brine (300 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crude compound was purified by column chromatography (100-200 silica) using 20% Ethyl Acetate in Hexane as eluent to afford 15 g (63% yield) of isomeric mixture of 7-bromo-6-methylquinoline Int-1 and 8-bromo-7- methylquinoline Int-1 A as a brown solid. The isomeric mixture of compound Int-1 and Int-IA (13 g) was separated by prep-HPLC purification to afford 5 g (21% yield) of Compound Int-1. (0689) MS (ESI) m/z 223.98 [M+H] . (0690) [0241] Int-1 : 1H NMR (400 MHz, CDC13): delta 8.87-8.84 (dd, J = 4.0 Hz, 1.2 Hz, 1H), 8.329-8.301 (d, J = 11.2 Hz, 1H), 8.27 (s, 1H), 7.97 (s, 1H), .53-1.51 (dd, J = 5.6 Hz, 5.2 Hz, 1H), 2.5 (s, 3H).

Statistics shows that 3-Bromo-4-methylaniline is playing an increasingly important role. we look forward to future research findings about 7745-91-7.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Bromide – Wikipedia,
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Electric Literature of 18087-73-5, A common heterocyclic compound, 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, molecular formula is C6H4BrN3, 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.

In a 100 ml two port in round bottomed flask, adding 3 – bromo imidazole [1, 2 – b] pyridazine (compound 11) (1g, 5.05mmol), Zn (CF3 SO2 )2 (5.0g,15 . 15mmol), 20 ml CH2 Cl2 , 8 ml H2 O. A system is cooled to 0 C after, slowly dropping t – BuOOH (2.5 ml, 25 . 2mmol) dichloro solution 5 ml. Then completing, maintain 0 C, stirring 3h after, the system moving to room temperature stirring 10h, TLC monitoring reaction process, after completion of the reaction, NaHCO adds by drops full and3 Solution to the system does not produce the bubble as the to. Add dichloromethane extraction, the combined organic phase, anhydrous Na2 SO4 Drying, and the pressure of the coils after silica gel, separation and purification through silica gel column (petroleum ether: ethyl acetate=20:1) to obtain compound 12 (0.13g, yield: 10%), compound 13 (0.40g, yield 30%).

The synthetic route of 18087-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin International Bio-pharmaceutical Joint Institute; Rao Zihe; Bai Cuigai; Chen Yue; Yang Cheng; Wang Lei; Zhong Chuanke; Li Huiying; Sun Tao; Li Jingpei; Wang Yang; (45 pag.)CN106883234; (2017); A;,
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7051-34-5, name is (Bromomethyl)cyclopropane, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C4H7Br

A solution of ethyl 1,3-dithiane-2-carboxylate (10.00 g, 52.00 mmol) and (bromomethyl)cyclopropane (7.02 g, 52.00 mmol) in dry DMF (20 ml_) was added dropwise over a period of 20 min to an ice cooled suspension of NaH (60% oil 15 dispension, 4.20 g, 104.00 mmol) in toluene (60 ml_). The mixture was stirred at rt overnight. Water (50 mL) was added and the mixture was extracted with EtOAc (2 x 50 ml_). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated to dryness. The residue was purified by column chromatography on silica gel (PE: EtOAc = 5:1) to give the title compound as a yellow oil.

The synthetic route of 7051-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX DISCOVERY VERWALTUNGS-GMBH; STEENECK, Christoph; KINZEL, Olaf; ANDERHUB, Simon; HORNBERGER, Martin; PINTO, Sheena; HERKERT, Barbara; HOFFMANN, Thomas; (129 pag.)WO2019/206800; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 111721-75-6, name is 2-Bromo-3-fluoroaniline, 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 111721-75-6, Computed Properties of C6H5BrFN

To a solution of 2-bromo-3-fluoroaniline (2.0 g, 11 mmol) in CH2Cl2 (50 mL) was added butyryl chloride (1.3 g, 13 mmol) and pyridine (1.7 g, 21 mmol) at 0 C. The mixture was stirred at room temperature for 24 h. Water (20 mL) was added and the mixture was extracted with CH2Cl2 (50 mL*3). The organic layers were dried anhydrous over Na2SO4 and evaporated under vacuum to give N-(2-bromo-3-fluorophenyl)butyramide (2.0 g, 73%), which was directly used in the next step.

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-3-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Bromide – Wikipedia,
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Electric Literature of 1073-06-9, 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. 1073-06-9, name is 1-Bromo-3-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1 (MS-Si):3-Fluoro-1-bromobenzene (1 mL, 11.6 mmol) was added to a mixture of magnesium (1.2 g,48.0 mmol) and a small amount (tip of a spatula) of iodine in dry tetrahydrofuran (20 mL)under organ atmosphere. After the color changed from bluish to colorless the remaining 3-fluoro-1-bromobenzene (3.3 mL, 38.4 mmol) was added and the mixture was stirred for 2 hat 50C. 1,4-cyclohexane monoethyleneketal (7.2 g, 50 mmol) was added and the mixturewas stirred at room temperature for 1 h. The reaction was quenched with saturatedammonium chloride, extracted with ethyl acetate and the separated organic layer was washed successively with water, brine; dried over anhydrous sodium sulfate and concentrated in vacuum to afford the crude intermediate. Purification by column chromatography over silica gel (60-1 20mesh) and using 15% ethyl acetate in pet ether as theeluent afforded 4.0 g (50%) of MS-Si as a white solid.

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-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROBIODRUG AG; HEISER, Ulrich; BUCHHOLZ, Mirko; SOMMER, Robert; DEMUTH, Hans-Ulrich; WO2014/140279; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary