Category: bromides-buliding-blocks

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 766-81-4 as follows. SDS of cas: 766-81-4

EXAMPLE 26; Preparation of 2-Amino-5-(5-chloro-2-methylthien-3-yl)-3-methyl-5-(3-pyrimidin-5-ylphenyl)-3,5-dihydro-4H-imidazol-4-one; Step a); Preparation of Compound 14; A mixture of 13 (3.17 g, 12.3 mmol), 3-bromophenylacetylene (2.44 g, 13.5 mmol; see MEC00775; dated Aug. 15, 2003), bis(triphenylphosphine)palladium(II) chloride (0.258 g, 0.360 mmol), copper(I) iodide (0.046 g, 0.240 mmol) and triethylamine (3.70 g, 36.8 mmol) in dimethylformamide (60 mL) was stirred at room temperature for 1.5 h. The mixture was diluted with ethyl acetate (300 mL), washed with water (2¡Á100 mL), brine (3¡Á100 mL), dried over sodium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography (silica, hexanes) to afford 14 as a yellow oil, which was a mixture of product and an unidentified by-product (which was removed during purification in the following step): APCI MS m/z 311 [C13H8BrClS+H]+.

According to the analysis of related databases, 766-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2007/4786; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 52548-00-2, 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 52548-00-2 as follows.

PREPARATIVE EXAMPLE 44; .Ph In aBH4; Step i; A mixture of 3-bromo-6-fluoro-o-xyle?e (25.37g, 432 mmol) in anhydrous CCI4 (250 mL) was treated with NBS (44.5g, 864 mmol) and benzoyl peroxide (310 mg) and then heated at reflux overnight. The mixture was cooled to 0 C and filtered, washing with hexanes. The filtrate was concentrated and chromatographed (hexanes) to give 44A as an colorless oil (41.57g, with minor mono-bromo impurities).

According to the analysis of related databases, 52548-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; MCCORMICK, Kevin D.; DONG, Li; BOYCE, Christopher W; DE LERA RUIZ, Manuel; ZHENG, Junying; WON, Walter S.; WO2010/42475; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 65185-58-2, These common heterocyclic compound, 65185-58-2, name is 2-Bromophenethylamine, 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.

Example 95 (4R,6R,7R)-1-(2-(2-bromo)phenyl)ethyl-4,7-di(tert-butyldimethyl-silyloxy)-4,5,6,7-tetrahydro-1H-indole-4,6-carbolacame (22). A solution of allylketone III-1 (example 2) (500 mg, 1.14 mmol) in dicloromethane (50 mL) was placed into a gas-washing bottle and cooled down to -78 C. in a dry ice bath. The mixture was then flushed with argon for 5 min, oxygen for 5 min and then with an oxygen/ozone mixture for 12 min The end of the reaction was indicated by a 5% potassium iodide/water solution turning orange, which was located at the exit. Afterwards, the reaction mixture was flushed for 10 min with argon to remove excess ozone. The gas-washing bottle was taken from the cooling bath and the content was slowly warming up to room temperature. The solvent was evaporated under reduced pressure to afford an oil (500 mg) which was dissolved in a 1:1 mixture of dichloromethane-acetic acid (2 mL). The resultant solution was treated at 0 C. with 2-(2-bromo)phenylethylamine (0.18 mL, 1.25 mmol) and it was stirred for 30 min The reaction mixture was neutralized with powdered sodium bicarbonate and it was diluted with dichloromethane and water. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. All the combined organic extracts were dried (anh. Na2SO4), filtered and concentrated under reduced pressure. The obtained residue was purified by columm chromatography over silica gel, previously neutralized with triethylamine-hexanes (5:95), using diethyl ether-hexanes (5:95) as cluent to afford compound 22 (150 mg, 23%) as a colourless oil. [alpha]D20=-109.0 (c1.3, in CHCl3). 1H NMR (250 MHz, CDCl3) delta 7.60-7.50 (m, 1H, ArH), 7.15-7.07 (m, 2H, 2*ArH), 6.60-6.55 (m, 1H, ArH), 6.50 (d, J=2.7 Hz, 1H, H-2), 6.14 (d, J=2.7 Hz, 1H, H-3), 4.50 (dd, J=5.5 and 3.5 Hz, 1H, H-6), 4.18 (d, J=3.5 Hz, 1H, H-7), 4.07 (m, 2H, NCH2), 3.29-3.19 (m, 1H, CHHAr), 3.09-2.93 (m, 1H, CHHAr), 2.47 (d, J=10.5 Hz, H-5eq), 2.38 (dd, J=10.5 and 5.5 Hz, H-5ax), 0.97 (s, 9H, C(CH3)3), 0.88 (s, 9H, C(CH3), 0.22 (s, 3H, CH3), 0.18 (s, 3H, CH3), 0.14 (s, 3H, CH3) and 0.14 (s, 3H, CH3) ppm. 13C NMR (63 MHz, CDCl3) delta 175.9 (C), 137.2 (C), 132.6 (CH), 130.8 (CH), 128.7 (CH), 127.9 (CH), 124.7 (C), 123.8 (C), 123.4 (C), 121.2 (CH), 103.5 (CH), 76.5 (CH), 74.2 (C), 64.1 (CH), 46.5 (CH2), 38.3 (CH2), 38.2 (CH2), 25.7 (2*C(CH3)3), 18.2 (C(CH3)3), 18.0 (C(CH3)3), -2.9 (CH3), -3.0 (CH3), -4.1 (CH3) and -4.3 (CH3) ppm. IR (KBr) 1799 (C=O) cm-1. MS (CI) m/z (%) 606 and 608 (MH-). HRMS calcd for C29H45O4NSi281Br (MH+): 608.2050; found, 608.2043.

Statistics shows that 2-Bromophenethylamine is playing an increasingly important role. we look forward to future research findings about 65185-58-2.

Reference:
Patent; UNIVERSIDADE DE SANTIAGO DE COMPOSTELA; US2011/313032; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1647-23-0,Some common heterocyclic compound, 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, molecular formula is C6H13Br, 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.

Into a 1 L round bottom flask equipped with a dropping funnel and a reflux condenser, 14.1 g (580 mmol) of shaved magnesium was added and 60 ml THF was added. Magnesium was etched slightly with a few iodine crystals, then 2 g of 1-bromo-3,3-dimethyl-butane was added and the mixture was locally heated. After the onset of Grignard formation, the remainder of 1-bromo-3,3-dimethyl-butane (total 88.1 g, 553 mmol) in 350 ml of THF was added within 20 minutes. The mixture was refluxed for 1.5 hours and then cooled to room temperature. In a separate 2 L round bottom flask, 63.9 g (464 mmol) of 2-chloro-benzonitrile and 141 mg (0.16 mol%) of copper (I) iodide were dissolved in 265 ml of THF. The Grignard solution was added dropwise over 30 minutes and the reaction mixture was refluxed for 3 hours. After standing overnight at room temperature, a mixture of 190 ml of water and 127 ml of concentrated hydrochloric acid was added very carefully to produce a strongly exothermic reaction. The mixture was stirred at 50 C. for 1 hour and the layers were separated. The aqueous layer was extracted twice with 150 ml each of toluene. The combined organic layers were washed twice with 2 M sulfuric acid, once with saturated sodium bicarbonate solution and once with saturated sodium chloride solution. After drying over magnesium sulfate, the solvent was evaporated in vacuo to give 103.8 g (quantitative) of the desired phenone as a slightly brown oil.

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-3,3-dimethylbutane, its application will become more common.

Reference:
Patent; LUMMUS NOVOLEN TECHNOLOGY GMBH; (91 pag.)JP6196581; (2017); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 4333-56-6, These common heterocyclic compound, 4333-56-6, name is Bromocyclopropane, 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.

To a stirred suspension of magnesium turnings (300 mg, 12.3 mmol) in THF (2.0 mL) was added commercially available cyclopropyl bromide (0.800 mL, 9.99 mmol) in THF (17.2 mL) dropwise at room temperature over 30 min. During this operation, the reaction continued refluxing without heating. After the addition of the halide was completed, the mixture was stirred at room temperature for 5 h. The concentration of this solution of 40 was determined by titration as shown below. Titration. After an exactly 0.150-mL aliquot of the Grignard solution of 40 was quenched with an exactly known volume (0.250 mL) of a 1.000 M HCl standard solution (purchased from Yoneyama Yakuhin Kogyo, Co., Ltd. (Japan)), the mixture was then titrated with a 0.500 M NaOH standard solution (purchased from Yoneyama Yakuhin Kogyo, Co., Ltd. (Japan)) (0.352 mL) with methyl orange as an indicator to determine its concentration to be 0.49 M. Thus, the yield of the Grignard reagent was 98% based on the halide. In several runs, the Grignard concentrations usually fell within a range between 0.48 and 0.51 M.

Statistics shows that Bromocyclopropane is playing an increasingly important role. we look forward to future research findings about 4333-56-6.

Reference:
Article; Sugano, Goshi; Kawada, Kojiro; Shigeta, Masayuki; Hata, Takeshi; Urabe, Hirokazu; Tetrahedron Letters; vol. 60; 13; (2019); p. 885 – 890;,
Bromide – Wikipedia,
bromide – Wiktionary

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. SDS of cas: 1073-06-9

General procedure: A mixture of a fluorinated aryl halide (2.0 mmol), a carbazole (0.5 mmol), and a base (2.0 mmol) in solvent (2 mL) was allowed to react under air atmosphere. The reaction mixture was heated to the specified temperature for 24 h. After reaction completion, the mixture was added to brine (15 mL) and extracted with CH2Cl2 (3 ¡Á 15 mL). The combined extract was concentrated under reduced pressure and the product was isolated by short chromatography on a silica gel (200-300 mesh) column.

The synthetic route of 1073-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Lei; Ji, Enhui; Liu, Ning; Dai, Bin; Synthesis; vol. 48; 5; (2016); p. 737 – 750;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 766-46-1, The chemical industry reduces the impact on the environment during synthesis 766-46-1, name is 2′-Bromophenylacetylene, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of sulfonyl azides 1 (0.6 mmol), o-bromo-phenylacetylenes 2 (0.5 mmol), aromatic amines 3 (0.55 mmol), and CuI (0.05 mmol) in DMSO (2 mL) in Schlenk tube was added TEA (0.5 mmol) slowly via a syringe. The reaction solution was stirred at room temperature under N2 for 2 h. The solution was then added to CuI (0.05 mmol), K2CO3 (1 mmol), and l-proline (0.2 mmol), and the mixture was stirred at 60 C under N2 for 4 h. The reaction mixture was partitioned between ethyl acetate and saturated aq NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with petroleum ether and ethyl acetate (6:1 to 9:1).

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

Reference:
Article; Jin, Hongwei; Zhou, Bingwei; Wu, Zhi; Shen, Yang; Wang, Yanguang; Tetrahedron; vol. 67; 6; (2011); p. 1178 – 1182;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 6911-87-1, 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. 6911-87-1 name is 4-Bromo-N-methylaniline, 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.

37.0 mg (0.2 mmol) of N-methyl-4-bromoaniline, 81.2 mg of ethyl bromodifluoroacetate (0.4 mmol), 2.5 mg (0.02 mmol) of cuprous acetate, 19.1 mg (0.04 mmol) of X-phos, 32.7 mg (0.2 mmol) of cesium carbonate were added to 2 mL of DMF solvent. The reaction was carried out at 110 C for 12 hours, after the reaction was completed, it was cooled, filtered, and the filtrate was evaporated. The solvent was removed and the residue was chromatographed on silica gel. It was washed with a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 8:1. The effluent was collected according to the actual gradient, detected by TLC, and the effluent containing the product was combined. The solvent was distilled off by a rotary evaporator. Drying in vacuo to give the yellow liquid -N-(4-bromophenyl)-N-methylformamide 26.0 mg, yield 61%.

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

Reference:
Patent; Wenzhou University; Zhang Xiaohong; Li Xiaofang; Zhang Xingguo; (15 pag.)CN108774147; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 30273-40-6,Some common heterocyclic compound, 30273-40-6, name is 4-Bromo-2,5-dimethylaniline, molecular formula is C8H10BrN, 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.

Preparation example 1 – Process (a) – compound (Na) to compound (VII) : 4′-tert-butyl-2,5- diotamethylbiotaphenyl-4-amiotane – intermediate (VII-P; The reaction is carried out using inert conditions (argon or nitrogen atmosphere, dry solvents). A suspension of 6.4 g (36.0 mmol) of (4-tert-butylphenyl)boroniotac acid, 6.0 g (30.0 mmol) of 4- bromo-2,5-diotamethylaniotaliotane, 29.3 g (90 mmol) caesium carbonate and 0.7 g (0.6 mmol) tetrakiotas(triotaphenylphosphiotan)palladiotaum in 75 ml of 1 ,2-diotamethoxyethan was stirred for 16 hrs at8O0C. At room temperature 25 ml of water and 75 ml of toluene were added. The organic layer was separated, the watery layer was again extracted using 75 ml of toluene. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Column chromatographie (cyclohexane / ethylacetate : 2/1 ) yielded 5.5g (21 ,7 mmol) 72 % of 4′-tert- butyl-2,5-diotamethylbiotaphenyl-4-amiotane (log P (pH 2.3) = 3.65.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2,5-dimethylaniline, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; WO2007/31512; (2007); A2;,
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. 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H2BrF3

2L three-necked flask, nitrogen protection, cast diisopropylamine, tetrahydrofuran 750g,Cooling -40 dropping n-butyl lithium, dropping temperature insulation reaction 30min, cooling to -78 , dropping raw materials3,4,5, -trifluorobromobenzene, dropping off,-78 insulation 2h.The temperature was raised to -60 C began dropping dimethyl sulfate,Maintain the temperature is not higher than -30 , the dropping was completed naturally rose to room temperature, incubated for 30min.Stop the reaction, the pump off the pressure of tetrahydrofuran,Add 400g of water,Dichloroethane extraction, the organic phase was washed again, concentrated under reduced pressure distillation, to obtain the final product 2-methyl-3,4,5-trifluorobromobenzene purity of 99.5% or more, a yield of 61%.

According to the analysis of related databases, 138526-69-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bengbu Zhong Shi Chemical Co., Ltd.; Yang Qing; Zhang Hao; Zhao Shimin; Xu Jianxiao; (4 pag.)CN105967974; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary