Tag: M.W=100-200

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., COA of Formula: C6H3BrF2

MTBE (60 mL) was charged to a 3-neck round bottom flask followed by bromo-2,3- difluoro-benzene (12 mL, 107 mmol). The solution was cooled in ice/salt bath. When the internal temperature reached 40C addition of i-PrMgClLiCl solution in THF (1.3M, 90.7 mL, 118 mmol) was started. The higher internal temperature during addition was 2 ¡ãC(bath temperature was -8¡ãC to -5¡ãC); addition time 17 mm. After addition was complete the reaction mixture was stirred at -5¡ãC to 0¡ãC for one hour. Tert-Butyl 3-oxopyrrolidine-1 – carboxylate (21 .8 g, 118 mmol) solution in MTBE (200 mL) was added to the reaction mixture at -4¡ãC to -2¡ãC during 15 mm. under vigorous stirring. The reaction mixture was stirred at -2¡ãC to 0¡ãC for 3 hours and then quenched by addition of 20percent aqueousammonium chloride solution (260 mL). The internal temperature rose from 0 ¡ãC to 15 ¡ãC during addition. The cooling bath was removed and the mixture was stirred at room temperature for 1 hour. Layers were separated and the aqueous phase was re-extracted with MTBE (120 mL). Combined organic extracts were washed with brine (160 mL) and water (2 x 120 mL). Organic layer was concentrated to approx. 120 mL volume. MTBE(120 mL) was added and solvent evaporated to 120 mL volume left. 120 mL of MTBE was added again and evaporated till 120 mL volume left. Cyclohexane (120 mL) was added and mixture concentrated until remaining volume was 120 mL. Co-evaporation with cyclohexane was repeated two times using 120 mL of cyclohexane each time. Final solution (160 mL) was stirred at room temperature. After 30 minutes, solution becamecloudy and crystallization started. The slurry was stirred for 2 hours at room temperature and then for 2 hours at 5 to 10 ¡ãC. Precipitate was filtered off, washed on the filter with cyclohexane (2 x 30 mL). Since the freezing of cyclohexane causes suction to dry on the filter, wet material was dried under vacuum at 40 00. There was obtained 22 g (69percent) of the Compound of Formula (VIa) as a solid and the purity thereof was 98 areapercent as determined by HPLC (UV detection at 220 nm). Content of the impurity Compound of Formula (VIII) as described herein was 1 .2percent as determined by HPLC (UV detection at220 nm).

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; INTEGRATIVE RESEARCH LABORATORIES SWEDEN AB; SONESSON, Clas; BUKSA, Maija; REINE, Inese; (76 pag.)WO2018/211080; (2018); A1;,
Bromide – Wikipedia,
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39478-78-9, name is 5-Bromo-2-methylaniline, 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. HPLC of Formula: C7H8BrN

Potassium phosphate (8.50 g, 40.0 mmol), L-proline (0.46 g, 4.00 mmol) and copper(l) iodide (0.38 g, 2.00 mmol) were added to a solution of 5-bromo-2- methylaniline (2.5 ml, 20.0 mmol) and morpholine (2.62 ml, 30.0 mmol) in dimethyl sulfoxide (15 ml). The reaction was heated to 120 0C under argon overnight. The reaction was then stirred at 120 0C for a further 6 hours. The reaction was allowed to cool before being diluted with water (-40 ml). The mixture was extracted with ethyl acetate (x3), the organic layer separated and washed with water (x2). The aqueous phase was then back extracted with ethyl acetate (x2). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash-silica gel chromatography to give crude 2-methyl-5-(4- morpholinyl)aniline (0.51 g), which was used without further purification.

The synthetic route of 39478-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; CHAMBERS, Laura Jane; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; STEADMAN, Jon Graham Anthony; WALTER, Daryl Simon; WO2010/125103; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 583-70-0, 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. 583-70-0, name is 2,4-Dimethylbromobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: to a suspension of magnesium powder (239 mg, 9.79 mmol) in dry THF(small amount) was added dropwise 1 -bromo-2,4-dimethylbenzene (1.64 g, 8.86mmol) diluted in dry THF (20 mL) and the reaction was heated at 40C. Aftercompletion of Grignard reagent, 2-methyl-N-[(5-methylfuran-2-yl)methylidene]propane-2-sulfinamide (995 mg, 4.66 mmol) diluted in THF (10mL) was added to the solution. The reaction mixture was stirred at rt overnight.Water was added to quench the reaction. The two layers were partitionated andthe organic layer was dried over Mg504, filtered and the solution wasconcentrated under reduced pressure. The crude material was purified by silicagel column chromatography using a gradient of hexanes/EtOAc ([5:1] to [4:1]) to afford N-[(2,4-di methyl phenyl)(5-methylfuran-2-yl)methyl]-2-methylpropane-2- sulfinamide (1 .27 g, 85%) as yellowish oil

The synthetic route of 2,4-Dimethylbromobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (82 pag.)WO2018/138354; (2018); A1;,
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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H7Br

A) Synthesis of N,N?-diphenyl-N,N?-dibenzocyclobutane-1,4-phenylenediamine (3) (0157) To a 500 ml, 3-neck round bottom flask equipped with a mechanical stirrer, nitrogen inlet, and reflux condenser (with nitrogen outlet), palladium (II) acetate (173 mg, 0.80 mmol) and tri(o-tolyl)phosphine (486 mg, 1.60 mmol) are added to 50 ml toluene. The mixture is stirred at room temperature under nitrogen until the palladium catalyst dissolves and the solution turns yellow. N,N?-diphenyl-1,4-phenylenediamine (10.0 g, 38.4 mmol), bromobenzocyclobutane (15.5 g, 76.8 mmol) and 200 ml toluene are added, followed by sodium t-butoxide (7.37 g, 76.8 mmol). Upon addition of the sodium t-butoxide the reaction turns black. The reaction is heated to reflux under nitrogen for 22 hours. The reaction is quenched by addition of 30 ml of 1 M aqueous HCl. The toluene solution is passed through basic alumina and the crude product is purified by recrystallization from a toluene/hexanes/methanol mixture. (0158) Yield=9.43 g (53 percent). 1H NMR (THF-d8) delta: 7.15 (t, 4H, Ar), 6.80-7.01 (m, 16H, Ar) 3.09 (s, 8H, -CH2CH2-) 13C-NMR (THF-d8) delta: 149.72, 148.26, 147.34, 144.18, 141.50, 129.92, 125.82, 125.76, 124.35, 123.61, 122.45, 121.06, 29.78.

According to the analysis of related databases, 1073-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; Gaynor, Scott; Inbasekaran, Michael; O’Brien, James J.; Welsh, Dean M.; (20 pag.)US9399702; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 74586-53-1, These common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-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.

General procedure: Conventional method: CDI (1.74 g, 0.01 mol) was added to dimethylacetamide solvent (1.0 mL) and were heated to 120-125C for 0.5 h. Cooled the solution to 60-65C and aniline (1.0 g, 0.01 mol) was added. After 1.5 h, HPLC analysis of the crude product showed that the reaction had proceeded to 100% conversion.The reaction solution was cooled to 20-25C and quenched with water (15 mL). The reaction mixture was extracted with isopropyl acetate (2 10 mL). The combined organic layer was washed with 1% aqueous HCl solution (2 10 mL),dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated under vacuum to give 1.3 g (90%) of N-phenylacetamide (Table 2, entry 1).

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chikkulapalli, Anil; Aavula, Sanjeev Kumar; Mona Np, Rifahath; Karthikeyan, Karthikeyan; Kumar C.H., Vinodh; Sulur G., Manjunatha; Sumathi, Shanmugam; Tetrahedron Letters; vol. 56; 24; (2015); p. 3799 – 3803;,
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. 399-94-0, name is 1-Bromo-2,5-difluorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-2,5-difluorobenzene

To a solution of 2-bromo-l,4-difluoro-benzene (3.01 g, 15.60 mmol, 1.20 Eq) in THF (15 mL) was added isopropyimagnesium chloride complex (2.27 g, 15.60 mmol, 1.20 Eq) at 0C dropwise under N2. The reaction was stirred at 15C for 1 hr to prepare (2, 5-difluorophenyl) magnesium bromide (23 mL). To a solution of tert-butyl (R)-4-((tert-butyldiniethyl.silyl)oxy)-2- oxopyrrolidine-l-carboxylate (4.10 g, 13.00 mmol, 1.00 Eq) in THF (50 mL) was added (2,5- difluorophenyl) magnesium bromide (23 mL) dropwise at ()C over 30 mins. The reaction mixture was stirred at 0C for 1 hr. Methanol (20 mL) was added to the mixture followed by NaBH4 (738 mg, 19.50 mmol, 1.50 Eq) at 0C. The mixture was stirred at 0C for 1 hr then poured into 10% aqueous NH4CI. The mixture was extracted with EtOAc (20 mL*2), the combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated. The crude product was purified by medium pressure liquid chromatography (MPLC) to give tert-butyl ((2R)-2-((tert- butyldimethylsilyl)oxy)-4-(2,5-difluorophenyl)-4-hydroxybutyl)carbamate (2.22 g, 5.14 mmol, 39.6% yield). 1H-NMR (400 MHz, CDC13) delta ppm 7.17-7.15 (m, 1H), 6.86-6.79 (m, 2H), 5.11-5.06 (m, 1H), 4.70 (br.s, 1H), 4.02-3.98 (m, 1H), 3.69 (br.s, 0.5H), 3.46 (br.s, 0.5H), 3.33-3.14 (m, 2H), 1.80-1.69 (m. 2H), 1.35 (s. 9H), 0.84-0.82 (9H, m), 0.04-0.03 (6H, m).

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; BLUEPRINT MEDICINES CORPORATION; WENGLOWSKY, Steven, Mark; BROOIJMANS, Natasja; MIDUTURU, Chandrasekhar, V.; BIFULCO, Neil; (206 pag.)WO2017/35354; (2017); A1;,
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. 583-70-0, name is 2,4-Dimethylbromobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H9Br

(e) (2,4-dimethyiphenyl)(phenyl)methanamine hydrochloride: To a suspension of Mg (1.32g, 55 nunol) in TI-iF (60 mnL) was added a catalytic aniount of 12 and ibrorno-2,4diniethylbenzene(0.5 g). The reaction was initiated by heating and then additional i-bromo-2,4-dimethylbenzene (8.75 g) was added dropwise. The mixture was stirred at it for 4 h under nitrogen. Benzonitrlie (5.15 g, 50 mmol) was added dropwise into the solution . After the addition, the reaction mixture was stirred at it for 16 Ii. Then the reaction was quenched by the addition 20 mL of MeOH,followed by NaBI-i, (1.9 g, 50 mniol) in portions. After stirring at rt for 5 h, the reaction was quenched by the addition of 20 nL water. Solvent was removed under reduced pressure. The residue was extracted with EtOAc (3 x 100 mE). IN aq. HCI was added to the combined organic layers during which a white solid precipitated. The white solid was collected by filtration (8.8 g, 84%). LCMS-Pi: 195 FM-NT-I2]4 IT-, = 1.232 mm. ?El NMR (500 MHz, DMSO-d6) 6 ppm9.15 (s, 2H), 7.55 (d,J 8.0 Hz, iT-i), 7.45 7.32 (in, 5Ff), 7.12 (d,.1 8.0 Hz, IT-i), 7.04 (s, iFi),5.64 5.62 (in, 1H), 2.27 (s, 3H), 2.22(s, 3H).

According to the analysis of related databases, 583-70-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; WO2013/19626; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, 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. Recommanded Product: (Bromomethyl)cyclopentane

Example 8A 2-(Trimethylsilyl)ethyl (1RS,2RS,5SR)-2-[4-(cyclopentylmethoxy)benzoyl]-5-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl]cyclopentanecarboxylate (racemate) To a solution of 80 mg (0.16 mmol) of the compound from Example 4A in 1.8 ml of acetonitrile were added 45 mg (0.32 mmol) of potassium carbonate and 32 mg (0.19 mmol) of (bromomethyl)cyclopentane, and the mixture was stirred under reflux overnight. Thereafter, a further 32 mg (0.19 mmol) of (bromomethyl)cyclopentane were added, and the mixture was stirred under reflux once again for 4 h. After cooling to RT, the mixture was diluted with water and extracted twice with dichloromethane. The combined organic phases were dried over magnesium sulphate and concentrated. The residue was purified by means of preparative HPLC (Method 7). 33 mg (36% of theory, 100% purity) of the title compound were obtained. LC/MS (Method 1, ESIpos): Rt=1.61 min, m/z=576 [M+H]+.

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

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMANN, Andreas; BROHM, Dirk; JOeRISSEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (91 pag.)US2017/22171; (2017); 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. 103-64-0, name is (2-Bromovinyl)benzene, A new synthetic method of this compound is introduced below., name: (2-Bromovinyl)benzene

At room temperature under a nitrogen atmosphere, to an appropriate amount of organic solvent (volume ratio 2: a mixture of methyl tetrahydrofuran and 2-propanol 1) were added successively compound 100mmol formula (I), 170mmol compound of formula (II), (III) compounds, 20mmol composite catalyst 300mmol formula (a 6mmolPd2 (dba) 3 with 14mmol trimethylphosphine (hexafluoroacetylacetonato mixture) of copper), 10mmol 300mmol gallium trichloride and an organic base2,4-lutidine, then warmed to 85 sufficiently stirred and incubated for 4 hours;After completion of the reaction, the reaction system was filtered, and the filtrate was cooled to room temperature, and then adjusting pH to neutral, and deionized water was added and washed thoroughly shaken, and extracted 3 times with chloroform, the organic phases combined, dried over anhydrous magnesium sulfate, distillation under reduced pressure, the resulting residue was purified by column chromatography on silica gel, ethyl acetate, acetone and the like in a volume ratio of washing liquid, to afford the compound of formula (IV of), in a yield of 97.6%

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; Li, Naiwen; (12 pag.)CN105218553; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. Application In Synthesis of (Bromomethyl)cyclopropane

In a round bottom flask,1 mmol of p-hydroxybenzaldehyde was added,20mL acetone dissolved,Stir evenly,3.0 mmol of potassium carbonate was added,A mixture of 1.0 equiv haloalkanes (bromomethylcyclopropane,1-bromo-3-methyl-2-butene,Bromo isobutane) in acetone solution 5 mL,The reaction was then allowed to reflux at an oil bath temperature of 65 C,The time and temperature of the reaction can be adjusted according to TLC detection,In order to carry out the reaction more thoroughly,Can be added in the middle of the reaction of 0.5equiv potassium carbonate,After the end of the reaction,First, the reaction solution was filtered under reduced pressure,The acetone solvent in the filtrate was distilled off under reduced pressure,The resulting mixture was then dissolved in methanol,Can be dissolved,Add 10 mL of the appropriate amount of saturated aqueous solution of potassium carbonate,Stirred at room temperature for 30 min,By potassium carbonate and unreacted 4-hydroxy acid esterification reaction,And then extracted with methylene chloride and saturated aqueous sodium chloride into the aqueous phase,According to the organic phase color to determine the number of extraction,Usually 3 times for the best,It is possible to remove the reaction substrate which does not participate in the reaction,The organic phase was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain an etherified product having a high purity.

The synthetic route of 7051-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TONGJI UNIVERSITY; WANG, HONGBING; WANG, ZHUO; (17 pag.)CN105967992; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary