Bromides-buliding-blocks

608-30-0, 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. 608-30-0, name is 2,6-Dibromoaniline, A new synthetic method of this compound is introduced below.

4-tert-Butylphenylboronic acid (4.81 g, 27.0 mmol) dissolved in ethanol (18 mL) and 2 M Na2CO3 (36 mL, 72 mmol) were added to a solution of 2,6-dibromoaniline (2.258 g, 9.0 mmol) in toluene (90 mL). To this solution, Pd(PPh3)4 (1.26 g, 1.0 mmol) was added. The mixture was heated to reflux for 72 h. After cooling to room temperature, the mixture was filtered and an excess of aqueous HCl was slowly added to the filtrate until no more white solid precipitated. The residue was suspended in diethyl ether after filtration and then an excess of 2 M Na2CO3 was slowly added until the solid was totally dissolved. The organic layer was dried over Na2SO4 and then the solvent was evaporated to give white solid (1.80 g, yield 56%). 1H NMR (500 MHz, CDCl3, delta in ppm): 7.47-7.52 (m, 8H, Ar-Hm), 7.15 (d, 2H, Ar-Ho), 6.89 (t, 1H, Ar-Hp), 3.95 (s,2H, NH2), 1.40 (s, 18H, CH3).

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; Pan, Huijie; Zhu, Liang; Li, Jiewei; Zang, Dandan; Fu, Zhisheng; Fan, Zhiqiang; Journal of Molecular Catalysis A: Chemical; vol. 390; (2014); p. 76 – 82;,
Bromide – Wikipedia,
bromide – Wiktionary

A common compound: 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 327-52-6

EXAMPLE H 3-Bromo-2,5,6-trifluorobenzaldehyde To a solution of 1-bromo-2,4,5-trifluoro benzene (25 g, 0.12 mol) in THF (200 mL) at -78 C. was added LDA (80 mL, 1.5 M) dropwise. The mixture was stirred at -78 C. for 1 hour, then N-formylpiperidine (16 g, 0.144 mol) was added in one portion and stirring continued for 2 hours. An additional 15 g of N-formylpiperidine was then added every 0.5 hour in 5 g portions. The reaction was quenched with 3N HCl (pH 3) at -78 C. The reaction was warmed to 0 C. and partitioned between H2 O and ether. The ether layer was dried and concentrated and the residue was distilled to provide 13 g (45%) of the desired aldehyde; bp 63-65 C. (0.2 mm).

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, 327-52-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Warner-Lambert Company; US5047538; (1991); A;,
Bromide – Wikipedia,
bromide – Wiktionary

38573-88-5, 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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 2Preparation of (4-bromo-2,3-difluorophenyl)trimethylsilaneDiisopropylamine (7.86 grams (g), 78 mmol) was dissolved in tetrahydrofuran (THF; 104 mL) and cooled to -75¡ã C. utilizing a dry ice/acetone bath.A solution of n-BuLi (2.5 M in hexanes; 22.80 mL, 57.0 mmol) was added dropwise, and the solution was again cooled to -75¡ã C. 1-Bromo-2,3-difluorobenzene (10 g, 51.8 mmol) was dissolved in THF (25.9 mL), and the solution was added dropwise keeping the temperature below -60¡ã C.The reaction mixture was then allowed to warm to -15¡ã C. before cooling again to -75¡ã C. TMSCl (7.29 mL, 57.0 mmol) was then added dropwise, and the reaction mixture was allowed to warm to 25¡ã C. and then concentrated under vacuum.The residue was partitioned between ethyl acetate (EtOAc) and H2O.The organic phase was washed twice more with H2O and concentrated.Kugelrohr distillation at 88¡ã C. provided the product in greater purity but an impurity was distilling at that temperature.Kugelrohr distillation of that purified distillate at 75¡ã C. led to purer product but some product was left in the pot.This process yielded the title compound as a clear oil (3.0 g, 21.83percent, 90percent purity): 1H NMR (300 MHz, CDCl3) delta 7.28 (ddd, J=7.8, 5.2, 1.3 Hz, 1H), 6.98 (ddd, J=8.0, 4.8, 1.9 Hz, 1H), 0.32 (s, 9H); EIMS m/z 264, 266.

The synthetic route of 38573-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epp, Jeffrey B.; Lowe, Christian T.; Renga, James M.; Schmitzer, Paul R.; Eckelbarger, Joseph D.; Guenthenspberger, Katherine A.; Siddall, Thomas L.; Yerkes, Carla N.; Fischer, Lindsey G.; Giampietro, Natalie C.; Kister, Jeremy; Roth, Joshua; US2013/5574; (2013); 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 1435-51-4 as follows. 1435-51-4

Example 23-Difluoromethyl-5-(2,3-difluoro-6-nitrophenoxy)benzonitrile (FIGURE 2;ROUTE B).step 7; – /?-Methoxybenzyl alcohol (12.4 kg, 89.8 mol) was added slowly to a mixture of potassium tert-butoxide (10.0 kg, 89.4 mol) in THF (78 L) allowing the reaction exotherm to raise the temperature to ca. 35 C. After stirring at 35 to 40 C for 0.5 h, 25 (21.4 kg, 84.3 mol) was added slowly allowing the reaction to exotherm to reach ca. 60 0C. After stirring at 60 C for 2 h the reaction was monitored by hplc. After cooling to RT, HOAc (ca. 600 g) and then water (30 L) was added and the phases separated. The aqueous phase was extracted with EtOAc (20 L) and the combined organic phases washed with a mixture of saturated brine (10 kg) and water (10 L). The organic phase was concentrated in vacuo (ca. 27 inches Hg, jacket temperature ca. 65 0C) to afford an oil. MeOH (ca. 43 kg) was added to form a biphasic mixture which was aged at 45 to 50 C. The product precipitated and the slurry was stirred until a uniform consistency was achieved. After cooling to RT, and aging overnight, the product was filtered off, washed with MeOH (9.8 kg), and dried under vacuum at 50 C to afford 26.06 kg of 40. The material remaining in the reactor and filter was dissolved in THF (ca. 10 L) and the solution evaporated to dryness on a rotary evaporator to afford an additional 3.44 kg (94% overall)

According to the analysis of related databases, 1435-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/145563; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

327-52-6, A common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

Dissolve 2,4,5-trifluorobromobenzene (10.5 g 49.8 mmol) in tetrahydrofuran (25 mL) with methyl tert-butyl ether(25 mL), cooled to -30 C, isopropyl magnesium chloride (4.8 g 46.5 mmol) was slowly added dropwise to the solution, stirred at -30 C for 10 min, and added with cuprous chloride (1.6 g 16.6 mmol). After stirring at -30C for 15 min, the compound of formula 3 (6.1 g 33.2 mmol) was dissolved in methyl tert-butyl ether (20 mL) and slowly added dropwise to the reaction system. The temperature rose from -30C to -3C within 3 h. At 10C, it was warmed to -5C over a further 3 h and reacted overnight at 0C. Saturated ammonium chloride (25 mL) was added to the reaction system, extracted with ethyl acetate (20 mL*1), washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and stirred with petroleum ether (50 mL) to obtain 15.6 g. Product 4, yield 90%.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Heding (Nanjing) Pharmaceutical Co., Ltd.; Li Wensen; (18 pag.)CN105017081; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 54879-20-8, name is 2-Bromo-3-methylaniline, molecular formula is C7H8BrN, 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. 54879-20-8

EXAMPLE 7 Preparation of 7-methyl-8-bromo-1-[(3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride STR33 2-Bromo-3-methylphenylhydrazine hydrochloride (23 g) was prepared as described for 2-bromo-4-methylphenylhydrazine hydrochloride in Example 4, except using 2-bromo-3-methylaniline as starting material. STR34 6-Methyl-7-bromotryptamine hydrochloride was prepared (2.42 g) as described for 5-methyl-7-bromotryptamine hydrochloride in Example 4, except using 2-bromo-3-methylphenylhydrazine hydrochloride as starting material. STR35 A suspension of azalactone (prepared as described in Example 1) (3.63 g, 14.7 mmol.) and 6-methyl-7-bromotryptamine hydrochloride (4.25 g, 4.21 mmol.) in 1N HCl (150 mL) was heated to reflux for 18 hours under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature, neutralized with saturated aqueous potassium carbonate solution and extracted with chloroform. The combined organic layers were concentrated under reduced pressure and the residue chromatographed on silica gel (ethyl acetate/0.2percent NH4 OH as eluent). The fractions containing product were pooled and concentrated under reduced pressure. The residue was dissolved in ethyl acetate containing 1percent methanol and treated with dry HCl.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 54879-20-8, its application will become more common.

Reference:
Patent; Eli Lilly and Company; US5635528; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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 51437-00-4. 51437-00-4

In the case of Q10-Br, the desired 2-fluoro-5-phenyl-toluene (S1=F) was prepared from phenylboronic acid and 2-fluoro-5-bromo-toluene via a Suzuki reaction, analogously to procedure A2. See scheme A3.

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 4-Bromo-1-fluoro-2-methylbenzene.

Reference:
Patent; Duphar International Research B.V.; US6225312; (2001); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

202865-83-6,Some common heterocyclic compound, 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, molecular formula is C7H6BrF, 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 of 1 -(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5- (methoxycarbonyl)-3-methyl-1H-pyrazol-4-ylboronic acid (50 mg, 0.10 mmol), 1-bromo-3- fluoro-5-methylbenzene (23 mg, 0.12 mmol), Pd(PPh3)4 (12 mg, 0.10 mmol), Na2003 (54 mg, 0.51 mmol) in degassed 1,4-dioxane and H20 (4:1, 2.1 mL) was heated at 85 C for 18 hours. LiOH (12.4 mg, 0.52 mmol) was added and the reaction was heated at 90 O under microwave radiation for 45 minutes. 1 N HCI (1 mL) was added, followed by water (5 mL) and the mixture was extracted with EtOAc (3x5mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by semi-prep H PLC-MS (column X-Bridge 30×50) using a solution of MeCN in water (containing 10 mM of NH4CO2H) (60 to 80%). The product was lyophylised and afforded the title compound (13 mg, 0.024 mmol, 24%) as a pale yellow solid. 1H NMR (500 MHz, DMSO) O 8.21 (d, J= 2.0 Hz, 1H), 8.02 (dd, J= 8.5, 2.0 Hz, 1H), 7.75 (d, J= 8.5 Hz, 1H), 7.13 (5, 1H), 7.11 (d, J= 9.9 Hz, 1H), 7.07 (d, J= 9.7 Hz, 1H),3.35 (hept, J= 6.7 Hz, 1H), 2.36 (5, 3H), 2.31 (5, 3H), 1.24 (d, J= 6.7 Hz, 6H); MS (mlz):536.0 [M+H].

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

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M. Arshad; CIBLAT, Stephane; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu, Jr.; SRIVASTAVA, Sanjay; SHIPPS, Gerald W.; COOPER, Alan B.; OZA, Vibha; KOSTURA, Matthew; LUTHER, Michael; LEVINE, Jedd; (253 pag.)WO2018/102452; (2018); A2;,
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 2606-51-1 as follows. 2606-51-1

General procedure: Benzyl bromide (1 g) in dry toluene (15 mL). To this tripheylphosphine (1.5 g) was added and the reaction mixture was refluxed for 1-3 h at 120 C to get the wittig salt as precipitate. It was filtered and washed with dry benzene (yield 62-87%).

According to the analysis of related databases, 2606-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Parihar, Swati; Kumar, Amit; Chaturvedi, Amit K.; Sachan, Naresh Kumar; Luqman, Suaib; Changkija, Bendangla; Manohar, Murli; Prakash, Om; Chanda; Khan, Feroz; Chanotiya; Shanker, Karuna; Dwivedi, Anila; Konwar, Rituraj; Negi, Arvind S.; Journal of Steroid Biochemistry and Molecular Biology; vol. 137; (2013); p. 332 – 344;,
Bromide – Wikipedia,
bromide – Wiktionary

626-40-4, 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. 626-40-4, name is 3,5-Dibromoaniline, This compound has unique chemical properties. The synthetic route is as follows.

Compound II (2.25 g, 10 mmol),Compound III (2.51 g, 10 mmol) andDiisopropylethylamine (DIPEA, 3.88 g, 30 mmol) was dissolved in 50 mL of dry xylene,Then heated to reflux under nitrogen,Until the reaction is complete (usually 5 hours).The reaction mixture was carefully poured into 200 mL of ice water,Stirred, extracted with 50 mL x 3 CH2Cl2,Combined extraction phase,Washed successively with 1% dilute hydrochloric acid (200 mL) and brine (100 mL), and dried over anhydrous sodium sulfate.The desiccant was removed by suction filtration and the filtrate was evaporated to dryness on a rotary evaporator to give compound IV, a white solid,

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Guangdong Sai Bo Technology Co., Ltd.; Guo Huijun; (8 pag.)CN106749368; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary