Category: bromides-buliding-blocks

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;,
Bromide – Wikipedia,
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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. 113170-72-2, name is 3-Bromo-5-(trifluoromethyl)benzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

A solution of 3-bromo-5-(trifluoromethyl)benzene-l, 2-diamine (2 g, 7.84 mmol), phenylboronic acid (1.9 g, 15.68 mmol), potassium carbonate (2.2 g, 15.68 mmol), [1,1?- bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (320 mg, 0.39 mmol) in dioxane (30 mL) and water(l0 mL) stirred overnight at 110 C in an oil bath. The resulting mixture was cooled to room temperature and then concentrated under vacuum. The residue was diluted with 50 mL water and extracted with 3×40 mL of ethyl acetate. The combined organic phases were washed with 100 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 : 10)) to afford 5- (trifluoromethyl)-[l,r-biphenyl]-2, 3-diamine (1.34 g, 68%) as yellow oil. MS: (ESI, m/z): 253[M+H]+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 113170-72-2.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); 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;,
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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;,
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Reference of 608-30-0, The chemical industry reduces the impact on the environment during synthesis 608-30-0, name is 2,6-Dibromoaniline, I believe this compound will play a more active role in future production and life.

This compound was prepared by modified literature procedures.11,12 A solution of NaNO2 (0.205 g,2.97 mmol) in H2O (1.5 mL) was added dropwise to a suspension of 2,6-dibromoaniline, 7c, (678 mg, 2.70 mmol) in concentrated aqueous HCl (2.6 mL, 12 M) at 0 C. The mixture was stirred at 0 C for 90 min. Additional NaNO2 (55 mg, 0.797 mmol) was added. The mixture was stirred for an additional 45 min at 0 C and then the resulting cold solution was added dropwise to a stirred solution of potassium ethyl xanthate (525 mg, 3.27 mmol) in H2O (0.65 mL) at 45 C through a glass pipet with a plug of glass wool. The reaction mixture was stirred for 30 min at this temperature and then allowed to cool to room temperature. The reaction mixture was extracted with diethyl ether (3×50 mL). The combined organic extracts were washed with 1 M NaOH solution (100 mL), water (3x 50 mL), brine (50 mL), dried over anhyd MgSO4, filtered and evaporated under reduced pressure. The resulting crude product was dissolved in ethanol (8 mL) and heated to reflux. Potassium hydroxide pellets (654 mg, 11.6 mmol) were added and refluxing continued overnight. After cooling to room temperature, the ethanol was evaporated under reduced pressure. The residue was dissolved in water and washed with diethyl ether (100 mL). The aqueous layer was acidified with 1 M HCl to pH 2 and extracted with diethyl ether (3 50 mL). The organic extracts were washed with water (50 mL), brine (50 mL), dried over anhyd MgSO4, filtered and evaporated under reduced pressure. The residue was purifiedby column chromatography on silica gel using hexanes as eluent to give 8b as a slightly yellow solid (518 mg, 72%). This compound always contains trace amounts of oxidized disulfide compound. Therefore, compound 8b was used in next step without further purification. 1H NMR (500 MHz, CD2Cl2) d 5.04 (s, 1H), 6.87 (t, J=7.0 Hz, 1H), 7.52 (d, J=7.0 Hz, 2H); IR (KBr) 1400, 1421, 1543, 2553(SH), 3064, 3458 cm1.

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, 2,6-Dibromoaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yamamoto, Takuhei; Ammam, Malika; Roberts, Sue A.; Wilson, George S.; Glass, Richard S.; Tetrahedron; vol. 72; 20; (2016); p. 2527 – 2534;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 7314-86-5,Some common heterocyclic compound, 7314-86-5, name is 1,3,5,7-Tetrabromoadamantane, molecular formula is C10H12Br4, 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 250ml three-necked flask equipped with a condenser tube5.0 g (ie 11.0 mmol) of tetrabromoadamantane and20 mL (ie, 165 mmol) of m-dibromobenzene,Condenser duct from the upper end connected to an inverted funnel 30% NaOH aqueous solution,To absorb the HBr produced by the reaction.Cold water bath at 5 ,To the reaction system was added 1.2g (ie, 4.5mmol) of AlBr3, stirring was continued under a cold water bath for 1 hour,Then remove the cold water bath,Return to room temperature for about 3 hours,The final reaction system was heated in an oil bath to 60 C for 4 hours,The reaction solution was cooled to room temperature,Pour into 100 mL of acidic ice water and stir for 1 h.After the ice is completely melted, 100 ml of methylene chloride is added to the mixture for extraction. The organic layer is washed with water until neutral, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and the filtrate is concentrated. The concentrated solution is then slowly added dropwise to 100 ml Methanol, precipitation,9.31 g of a pale yellow solid was obtained in a yield of 79%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3,5,7-Tetrabromoadamantane, its application will become more common.

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; Chen Jinping; Li Yi; Yu Tianjun; Zeng Yi; (18 pag.)CN107266319; (2017); A;,
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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 54962-75-3 as follows. Product Details of 54962-75-3

3-bromo-5-trifluoromethylaniline (720 mg, 5 mmol) was dissolved in concentrated hydrochloric acid, cooled to -10 C, and an aqueous solution of sodium nitrite (380 mg, 5.5 mmol) was added dropwise to react for 2 h. Cooled to -30 C, dropped into a concentrated hydrochloric acid solution of SnCl2 (3.40g, 15mmol) pre-cooled to -30 C, reacted at -20 C for 1h, warmed to room temperature, filtered, and dried to give 805 mg of a pale yellow solid, yield 100%.

According to the analysis of related databases, 54962-75-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Cui Guonan; Lai Fangfang; Zhou Jie; Ji Ming; Wang Xiaoyu; Du Tingting; Li Ling; Jin Jing; (144 pag.)CN110483366; (2019); A;,
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;,
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bromide – Wiktionary