Tag: M.W=100-200

1647-23-0, A common compound: 1647-23-0, name is 1-Bromo-3,3-dimethylbutane, 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.

In an oven-dried flask, a suspension of magnesium turnings (1.82 g, 75 mmol) in THF (40 mL) is treated with molecular iodine (254 mg, 1 mmol). To this mixture is added twenty drops of a solution of 3,3-dimethylbutyl bromide (7.14 mL, 50 mmol) in THF (10 mL) via a fitted separatory funnel. The resulting mixture is heated to reflux, followed by addition of the remaining 3,3-dimethylbutyl bromide solution. The reaction mixture is allowed to reflux for 1h, cooled to rt, and used as is (1.0 M solution of 3,3-dimethylbutylmagnesium bromide in THF, 50 mmol)

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

Reference:
Patent; ELI LILLY AND COMPANY; EP1856090; (2009); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

38573-88-5, These common heterocyclic compound, 38573-88-5, name is 1-Bromo-2,3-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.

Under nitrogen atmosphere, diisopropylamine (25.2 g) was dissolved in THF (130 mL) and cooled to -70 ¡ã C. or lower. To the solution, a 1.6 M butyl lithium / hexane solution (130 mL) was added dropwise at a rate such that the internal temperature did not reach -65 ¡ã C., and then the mixture was stirred at -70 ¡ã C. or less for 30 minutes. Subsequently, a solution prepared by dissolving 2,3-difluorobromobenzene (40 g) in THF (150 mL) was added dropwise to the stirring reaction solution at a rate such that the internal temperature did not exceed -65 ¡ã C., For 1 hour. Subsequently, a solution of DMF (22.7 g) dissolved in THF (220 mL) was added dropwise at a rate such that the internal temperature did not become -65 ¡ã C. or higher, followed by stirring at -70 ¡ã C. or lower for 1 hour, then slowly And the mixture was heated to room temperature. 10percent hydrochloric acid and toluene were added to the reaction solution, the organic layer was separated, and the organic layer was washed with saturated brine. Sodium sulfate was added to the organic layer after washing and dried, and then the solvent was distilled off under reduced pressure to obtain a crude product (44.9 g) of 4-bromo-2,3-difluorobenzaldehyde.

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 38573-88-5.

Reference:
Patent; DIC CORPORATION; TOJO, KENTA; KUSUMOTO, TETSUO; TAKATSU, HARUYOSHI; (13 pag.)JP6019595; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

1422-54-4, 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. 1422-54-4, name is 2-Bromo-6-fluorotoluene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 42 Preparation of (4-bromo-2-fluoro-3-methylphenyl)dimethyl(phenyl)silane To a 100 mL flask charged with THF (30 mL) was added diisopropylamine (1.285 g, 12.70 mmol). The reaction flask was cooled to -78 C. in a dry ice acetone bath and n-butyllithium (0.746 g, 11.64 mmol) was added. After 40 min of stirring at -78 C., 1-bromo-3-fluoro-2-methylbenzene (2 g, 10.58 mmol) in THF (10 mL) was added dropwise. Once an additional 40 min at -78 C. had passed, chlorodimethyl(phenyl)silane (5.42 g, 31.7 mmol) was added in one portion, the dry ice/acetone bath was removed and the reaction mixture was allowed to warm to room temperature. The reaction mixture was neutralized with a 5% HCl solution and diluted with water (200 mL). The aqueous solution was washed with EtOAc (200 mL*2). The combined organic layers were dried over Na2SO4. Following filtration, the organics were concentrated and the resulting residue was purified by flash chromatography with a gradient eluent system of hexanes and EtOAc to yield a clear oil as a mixture of products that contained (4-bromo-2-fluoro-3-methylphenyl)dimethyl(phenyl)silane which was used without further purification (850 mg): ESIMS m/z 324 ([M+H]+1).

The synthetic route of 1422-54-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; ECKELBARGER, Joseph D.; EPP, Jeffrey B.; FISCHER, Lindsey G.; GIAMPIETRO, Natalie C.; KISTER, Jeremy; PETKUS, Jeffrey; ROTH, Joshua; SATCHIVI, Norbert M.; SCHMITZER, Paul R.; SIDDALL, Thomas L.; YERKES, Carla N.; US2014/274703; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 2270-59-9, name is 5-Bromo-2-methylpent-2-ene, 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 2270-59-9. 2270-59-9

EXAMPLE 5 2-Methyl-5-nitro-2-pentene 5-Bromo-2-methyl-2-pentene (120 g, 0.736 m) is added dropwise to a solution of sodium nitrate (60.9 g, 0.883 m) in dimethylsulfoxide (700 ml) at room temperature under nitrogen. The mixture is stirred for 1 hour and treated with water (500 ml) and petroleum ether (1 l). The organic layer is dried (Na2 SO4) and evaporated in vacuo to give a pale yellow liquid (80.7 g). This material is purified by column chromatography on silica gel (800 g, petroleum ether) to give 2-methyl-5-nitro-2-pentene as a colorless liquid (45.4 g, 48%). ir (neat) 1550 cm-1; nmr (CDCl3) delta: 1.70 and 1.73 (both 0,6H, (CH3)2 C=C<), 2.5~2.93(m, 2H, CH2 4.35 (t, J=8 Hz, 2H, --CH2 --CH2 --NO2), STR7 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 5-Bromo-2-methylpent-2-ene. Reference:
Patent; Ortho Pharmaceutical Corporation; US4177194; (1979); A;,
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

51436-99-8, 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 51436-99-8 as follows.

Add sodium hydride (60% dispersion in oil, 880 mg, 22 mmol) to a solution OF 4- HYDROXY-L-METHYL-PIPERIDINE (2. 304 g, 20 mmol) in DMF (12 mL), stir. After 30 min., add 4-BROMO-2-FLUOROTOLUENE (4.159 g, 22 mmol) and heat at 70 C. After 21 hr. , quench the reaction with saturated NAHC03 solution, extract with ether three times, combine the organic layers, wash with saturated NaCl solution, dry over NA2SO4, filter and concentrate to give a residue. Purify by chromatography (silica gel, eluting with 6% 2M NH3- methanol in CH2CI2) provides of the title compound as a slightly yellow oil (3.90 g, 69%). Mass spectrum (ion spray): m/z = 284.0 (M ;’H NMR (CDCI3, ppm): 7.01 (m, 3H), 4.35 (m, 1H), 2.66 (m, 2H), 2.36 (m, 2H), 2.34 (s, 3H), 2.19 (s, 3H), 2.03 (m, 2H), 1.85 (m, 2H).

According to the analysis of related databases, 4-Bromo-2-fluorotoluene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/94380; (2004); 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. 1003-98-1 name is 2-Bromo-4-fluoroaniline, 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. 1003-98-1

General procedure: 4.2 General procedures: A. Microwave. Neat samples of amine (1.00 mmol) and carboxylic derivative (methyl ester or acid, 1.00 mmol) and DABAL-Me3 (202 mg, 0.8 equiv) were placed in a 5 mL microwave vial and dry THF added (1 mL) under a blanket of argon. For coupling partners containing acidic hydrogens additional DABAL-Me3 (total of 410 mg, 1.6 equiv) was used. The vial was promptly capped and placed in a CEM Discover microwave reactor. After irradiation (290 W, 130 C, 8 min) and programmed cool down (ca. 20 min). The reactions were quenched by cautious addition of HCl (2 M, 4 mL) or aqueous solutions of Rochelle salt (saturated potassium sodium tartrate, 4 mL) (CARE: methane liberated). Extraction with dichloromethane, drying (MgSO4) and evaporation frequently provided the pure products directly. If purification was required column chromatography 3:2 to 2:3 hexane:EtOAc was used for amides lacking highly polar functional groups (CH2Cl2 with 2 % v/v MeOH was used for amides bearing pendant amines, alcohols and other polar functional groups).

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

Reference:
Article; Dubois, Nathalie; Glynn, Daniel; McInally, Thomas; Rhodes, Barrie; Woodward, Simon; Irvine, Derek J.; Dodds, Chris; Tetrahedron; vol. 69; 46; (2013); p. 9890 – 9897;,
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

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

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