Bromides-buliding-blocks

A common compound: 51554-93-9, name is 1-Bromo-4-octylbenzene, 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. 51554-93-9

To synthesize intermediate compound 16d, n-BuLi (2.5 M in hexane, 146 muIota_, 0.364 mmol) is added dropwise to a solution of 1 -bromo-4-octylbenzene (16a) (94 mg, 0.350 mmol) in THF (0.53 ml_) at -78 C. After stirring for 0.5 h, 16c (40 mg, 0.14 mmol) in THF (0.1 ml_) is added to the mixture, and the solution is stirred for an additional 2 h at-78 C. The reaction is then warmed to -40 C and stirred overnight. The reaction mixture is quenched at -40 C with saturated NH4CI solution and allowed to warm to room temperature. The organic layer is separated and the aqueous layer is extracted three times with CH2CI2. The combined organic layers are washed with brine, dried over MgS04 and filtered. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (hexane: EtOAc, 12: 1 to 8: 1 ) to give compound 16d (21 mg, 32 %) as a slightly yellow oil.

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, 51554-93-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; THE UNIVERSITE DE MONTREAL; EDINGER, Aimee; HANESSIAN, Stephen; (172 pag.)WO2017/53990; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 38573-88-5 name is 1-Bromo-2,3-difluorobenzene, 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. 38573-88-5

(6S,9R)-6-(2,3-Difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one. See Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. In an oven-dried 1 L flask was Sodium tert-butoxide (13.19 g, 137 mmol), PALLADIUM(II) ACETATE (0.948 g, 4.22 mmol), and 2-(Dicyclohexylphosphino)-2′-methylbiphenyl (1.539 g, 4.22 mmol) weighed in a nitrogen bag. (R)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (35.21 g, 106 mmol), Toluene (106 mL) (degassed in the original bottle by nitrogen gas), and 1-bromo-2,3-difluorobenzene (14.18 mL, 127 mmol) were added under nitrogen. The flask stirred at 80¡ã C. in a pre-heated oil bath for 20 h. Volatiles were stripped off and the residue was partitioned between EtOAc (400 ml) and water (400 ml). The layers were separated. The aqueous layer was extracted with EtOAc (50 ml). The combined organic layer was washed with brine, dried and concentrated to a dark oil. It was passed through a plug of silica gel (loaded with CH2Cl2 and eluted with EtOAc/hexane up to 30percent EtOAc). The crude product was obtained as a dark red oil (86percent mass recovery),. 1H NMR showed approximately 6/1 ratio of the desired trans isomer to the cis isomer. MS(ESI)[M+H+]=446.21.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,3-difluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/258866; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, 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. 28342-75-8

General procedure: E1 (3.00 equivalents), E2 (1 .00 equivalents) and E3 (1 .00 equivalents) were dissolved in dry DMF, NaH (6.00 equivalents) was added and the reaction mixture was stirred at 50 ¡ãC over night. Subsequently, NaH (3.00 equivalents) was added to the reaction mixture. The reaction mixture was poured on water and extracted repeatedly with dichloromethane. The combined organic layer was dried over sodium sulfate (Na2S04). The solvents were evaporated under reduced pressure to obtain Z1. Z1 (1 .00 equivalents) was dissolved in tert-butylbenzene and the solution was cooled to -30 ¡ãC. tert-Butyllithium (‘BuLi) (4.00 equivalents) was added dropwise and the reaction mixture was slowly heated up to 0 ¡ãC. After stirring for 30 minutes at 0 ¡ãC, the reaction mixture was cooled again to -30 ¡ãC. (0229) A solution of boron tribromide (BBr3, 2.2 equivalents) was added dropwise, the bath was removed and the reaction mixture was allowed to warm to room temperature (RT). Subsequently, the reaction mixture was heated at reflux at 120 ¡ãC for 5h. Volatiles were removed under reduced pressure to obtain Z3. (0230) A solution of Grignard compound/compounds [R1MgBr (1 .5 equivalents) / R2MgBr (1.5 equivalents)] was added dropwise to Z3 over a period of 30 min. After stirring for 1 h, MeOH was added to the reaction mixture and the solvents were evaporated under reduced pressure. The residue was dissolved in toluene and filtered with a pad of silica gel (toluene was used as eluent). The solvent was removed under reduced pressure. The crude product was dissolved in a minimum amount of toluene and then a small amount of heptane was added. The resulting precipitate was filtered to obtain P1 as a solid product.

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 28342-75-8.

Reference:
Patent; CYNORA GMBH; SEIFERMANN, Stefan; (41 pag.)WO2019/52940; (2019); 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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, A new synthetic method of this compound is introduced below., 38573-88-5

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 3b (1.22 g, 5 mmol) was dissolved in 20 mL of tetrahydrofuran under stirring under an argon atmosphere, and 1-bromo-2,3-difluoro-benzene (0.97 g, 5 mmol), tetrakis (triphenylphosphine) palladium (0.17 g, 0.15 mmol) and 7 mL of sodium hydroxide solution (2M) were then added to the solution. Upon completion of the addition, the reaction system was stirred at 75¡ãC in an oil bath overnight. The reaction was completed until TLC showed the disappearance of starting materials. The reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 mL*3). The combined organic extracts were washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to give the title compound 4-(2,3-difluoro-phenyl)-1H-indole 3c (800 mg, yield 70percent) as a white solid. MS m/z (ESI): 228.4[M-1]

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; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2179998; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

The chemical industry reduces the impact on the environment during synthesis 7766-50-9, name is 11-Bromo-1-undecene, I believe this compound will play a more active role in future production and life. 7766-50-9

p-Benzenediol (Hydroquinone, defined as BP1 here) (2.2 g,20 mmol) and sodium hydroxide (2.4 g, 60 mmol) were dissolved in 120 mL DMF in a 250-mL round bottomed Schlenk flask, then themixture was stirred for 30 min, and a solution of 11-bromo-1-undecene (12 g, 51.5 mmol) in DMF (120 mL) was added dropwise over 10 min. The resulting reaction mixture was heated at 70 C and left stirring for more than 8 h. Subsequently, the reaction was cooled to RT and quenched with addition of diethyl ether (100 mL) and water (100 mL). The aqueous phase was extracted with diethyl ether (300 mL 2), and the combined organic fractions were washed with brine and dried over MgSO4 and concentrated. The residue was recrystallized from EtOH twice to obtain 6.1 g BP1-M1. Yield: 74%.

The chemical industry reduces the impact on the environment during synthesis 7766-50-9. I believe this compound will play a more active role in future production and life.

Reference:
Article; Song, Shaofei; Miao, Weijun; Wang, Zongbao; Gong, Dirong; Chen, Zhong-Ren; Polymer; vol. 64; (2015); p. 76 – 83;,
Bromide – Wikipedia,
bromide – Wiktionary

766-81-4, 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.

Step 2) 1-Bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene To a solution of 3-bromophenylacetylene (9.1 g, 50.26 mmol), TEA (22.4 g, 221 mmol, 30.8 mL), bis(triphenylphosphine)dichloropalladium(II) (1.41 g, 2.01 mmol), and CuI (230 mg, 1.2 mmol) in DMF (60 mL) was added 4-iodo(difluoromethoxy)benzene (10.85 g, 40.21 mmol) at room temperature. The reaction mixture had gotten warm after the addition was completed. The mixture was stirred for 4 h then the mixture was portioned between EtOAc and water. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated over 40 g Celite. Flash chromatography (SiO2, Hexanes) gave 12 g, 92%, of the title compound as a yellow oil that had crystallized into a solid after being undisturbed for 3d. 1H NMR 500 MHz (DMSO-d6) delta 7.34 (dt, 2H, J=8.92 Hz, 4.70 Hz); 7.42 (t, 1H, 72.99 Hz); 7.54 (t, 1H, J=7.88 Hz); 7.85-7.88 (m, 1H); 7.94-7.97 (m, 1H); 8.00 (dt, 1H, J=8.93 Hz, 4.87 Hz); 8.04 (t, 1H, J=1.80 Hz). Step 2: 1-Bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene To a mixture of 1-bromo-3-ethynylbenzene (9.1 g, 50.26 mmol), TEA (22.38 g, 30.8 mL, 221.1 mmol), PdCl2(ACN)2 (1.41 g, 2.01 mmol) and DMF (60 mL) was added 4-iodo(difluoromethoxy)benzene (10.85 g, 40.21 mmol). The reaction mixture became warm after the addition was completed. The mixture was stirred for 4 h. Then it was poured into water and diluted with EtOAc. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated onto 40 g Celite. Flash chromatography (SiO2, Hexanes) provided 12 g, 92%, of the title compound as a yellow oil that crystallized into a yellow solid upon standing. 1H NMR 500 MHz (CDCl3) delta6.51 (t, J=73.49 Hz, 1H); 7.08 (dd, J=1.27 Hz, 7.65 Hz, 2H); 7.19 (t, J=7.89 Hz, 1H); 7.40-7.46 (m, 2H); 7.47-7.51 (m, 1H); 7.64 (t, J=1.63 Hz, 1H)

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

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

955959-84-9, A common heterocyclic compound, 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, molecular formula is C18H11BrO, 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.

Compound 1) d.) 500 mg (1.55 mmol) 4-(4-bromophenyl)dibenzofuran, 760 mg (1 .70 mmol) 2-(9H-carbazol-3- yl)-6-phenyl-benzimidazolo[1 ,2-a]benzimidazole, 990 mg (4.64 mmol) potassium phosphate tribasic, 60 mg (0.31 mmol) copper iodide in 10 ml dioxane are stirred under nitrogen at 100¡ãC. 1.24 g (36.1 mmol) cis, trans 1 ,2-diaminocyclohexane are added. The reaction mixture is stirred for 48 h. The reaction mixture is poured in methanol. The product is filtered off and is washed with water, methanol 10 percent tatraic acid. Column chromatography on silica gel with chloroform gives the product. Yield 690 mg (65 percent) MS (APCI(pos), m/z): 691 (M+1).

The synthetic route of 955959-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; KAWAMURA, Masahiro; NAGASHIMA, Hideaki; (314 pag.)WO2017/56052; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 24358-62-1 name is 1-(4-Bromophenyl)ethylamine, 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. 24358-62-1

Library Protocol I To a 0.2M solution of 5-(4,4, 5,5-tetramethyl- 1, 3,2-dioxaborolan-2-yl)-2-[( 1 -{[4-(trifluoromethoxy) phenyl]acetyl}piperidin-4-yl)oxy]pyridine-3-carboxamide (Preparation 13, 500 pL, 100 pmol) in DMF was added a 0.2M solution of compounds of formula (IV) (500 pL, lOOpmol) in DMF with argon purging. A 2M solution of cesium carbonate (100 pL, 200 pmol) in degassed water was added followed by tetrakis(triphenylphosphine)palladium (0) (5.7 mg, 5 pmol) and the reaction was heated to 11000 under microwave irradiation for 15 minutes. Thereaction was cooled and concentrated in vacuo. the residue was dissolved in DMSO (1 mL) and purified using preparative HPLC using one of the Purification Methods (PM) below:

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Bromophenyl)ethylamine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

The chemical industry reduces the impact on the environment during synthesis 5433-01-2, name is 1-Bromo-3-isopropylbenzene, I believe this compound will play a more active role in future production and life. 5433-01-2

3-isopropyl-benzonitrile 5.15 g (25.87 mmol) m-bromo-isopropyl-benzene and 2.69 g (30.04 mmol) copper cyanide are stirred in 2.50 ml of pyridine for 24 hours at 180 C. Then 15 ml of water, 15 ml of toluene and 15 ml conc. ammonia solution are added, then the mixture is extracted. The organic phase is dried and evaporated to dryness. Yield: 5.00 g (100% of theoretical)

The chemical industry reduces the impact on the environment during synthesis 5433-01-2. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Maier, Udo; Grauert, Matthias; Hoffmann, Matthias; Hoenke, Christoph; Joergensen, Anne T.; Pautsch, Alexander; Brandl, Trixi; Breitfelder, Steffen; Scheuerer, Stefan; Erb, Klaus; Pieper, Michael; Pragst, Ingo; US2007/259855; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

52997-43-0, 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. 52997-43-0, name is 7-(Bromomethyl)pentadecane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The general procedure (Table 1, entry 5 and 6) for the synthesis of alkylation of aniline (N-alkylation) and phenol (O-alkylation) is as follows. A two neck flask with a three-way stopcock and a rubber septum was charged with aniline (4 mmol, 0.373 g), 1-bromododecane (15 mmol, 3.74 g), K2CO3 (8 mmol, 1.11 g) and dry DMF (3.0 mL). The flask was heated at 120 C overnight. The first posttreatment: After checking of TLC and 1H NMR spectrum (Figure S3(a)), KOtBu (12 mmol, 1.346 g) was added to the flask at room temperature, then the mixture was heated to reflux overnight. The reaction was quenched by the addition of sat. NH4Cl aqueous solution, extracted into CH2Cl2 (50 ¡Á 3 mL), washed successively with water, brine, dried (anhydrous Na2SO4) and concentrated by rotary evaporator to afford the reaction mixture (including target dialkylated aniline and corresponding olefin, Figure S3(b)).The second posttreatment: Since the N-alkylation was almost quantitative reaction, the expected amount of olefin in the mixture was equal to the excess amount of starting alkylhalide (7.0 mmol in the above case). It could be assumed that 7.0 mmol of olefin should be treated with the small excess of 9-BBN (10.5 mmol, 1.5 eq vs olefin). A two neck flask with a three-way stopcock and a rubber septum was charged with the above reaction mixture and dry THF (20 mL). 0.5 M 9-BBN in THF (10.5 mmol, 21 mL) was added to the flask at 0 C and then the flask allowed to warm to room temperature and stirred for one hour. To quench the remaining 9-BBN in the reaction, aminoalcohol (2-dimethylaminoethanol, 4.5 mmol, 0.405 g) was added to the flask and stirred for another one hour. The final reaction mixture was quenched by the addition of water (5 mL), extracted into EtOAc (50 ¡Á 3 mL), washed successively with water, brine, dried (anhydrous Na2SO4) and concentrated by rotary evaporator to afford the crude mixture (Figure S5(a)). The third post-treatment: The crude product was purified by short silica-gel column chromatography (5 cm (diameter of column) ¡Á 10 cm (length of deposition of silicag-gel was enough for this scale) with n-hexane as eluent to give the dialkylated aniline (Figure S5(b)).

The synthetic route of 7-(Bromomethyl)pentadecane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Okamoto, Ken; Lu, Fengniu; Nakanishi, Takashi; Bulletin of the Chemical Society of Japan; vol. 91; 8; (2018); p. 1258 – 1263;,
Bromide – Wikipedia,
bromide – Wiktionary