Tag: M.W=100-200

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. 1124-14-7, name is 1-Bromo-4-cyclopropylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H9Br

In a flame dried flask under N2 blanket, compound D (1.5 g, 4.9 MMOL) was dissolved in dry THF (30 mL) and COOLED TO-78C. N-BUTYL lithium (1.9 M in hexanes, 5.4 mL, 9.7 MMOL) was added followed after 45 min by compound E (1.27 g, 6.3 MMOL). The cold bath was removed after 2 h and the reaction mixture was allowed to warm to rt over 45 minutes then quenched with aq NH4CI. EtOAc (30 mL) was added to dilute the reaction mixture. The reaction mixture was washed with brine (100 mL x 2). The organic layer was dried over NA2SO4 and then concentrated to dryness. The crude material was purified via sgc (25% EtOAc/Hexanes) to give 545 mg (27%) of compound F. Compound i (120 g, 1.0 mml) was dissolved in CH2CI2 (1.2 L) with HG20 (6.0 g, 14.4 MMOL) and K2CO3 (24.0 g, 0.17 mol) and cooled to-30 C. Br2 (85.2 g, 1.1 mol) was added over 10 min period of time. The reaction mixture was stirred at-30 C for 4.5 h. The reaction mixture was washed with H20 (1 L) and brine (1 L). The organic layer was dried over NA2SO4 and concentrated to dryness. The crude material was distilled under reduced pressure to give 103.8 g (52%) of compound ii. In a flame dried flask under N2 blanket, compound ii (6.0 g, 30.5 MMOL) was dissolved in dry THF (30 mL) and cooled TO-78 C. A solution of n-butyl lithium (1.75 M in hexanes, 17.4 mL, 30.5 MMOL) was added and the reaction mixture was stirred for 20 min. S02 was bubbled in the reaction for 20 min. It was slowly warmed up to rt. CH2CI2 (50 mL) was added and the mixture was reacted with NCS (5.0 g, 37.4 MMOL) at rt overnight. The reaction mixture was washed with brine (100 mL x 2). The organic layer was dried over NA2SO4 and then concentrated to dryness. The crude material was purified via sgc (5% EtOAC/Hexanes) to give 3.65 g (55%) of compound II. To a round-bottom flask was added compound iii (3.0 g, 13.8 MMOL) and KF (2.4 g, 41.4 MMOL) followed by addition of acetone (50 mL) and water (30 mL). The reaction mixture was stirred at room temperature overnight. The solvent was then removed. Methylene chloride (40 mL) was added and it was washed with brine (40 mL). The organic layer was dried over NA2SO4 and then concentrated to dryness to give 2.77 g (100%) of compound E.

The synthetic route of 1124-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2004/48322; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 35354-37-1, name is 1-Bromo-5-methylhexane, 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. category: bromides-buliding-blocks

Example 145 (+-)-4-(3-Ethanesulfonylaminophenyl)-trans-3,4-dimethyl-N-(5-methylhexyl)piperidine To a stirred solution of (+-)4-(3-ethanesulfonylaminophenyl)-trans-3,4-dimethylpiperidine (Preparation 39, 120 mg, 0.4 mmol) in N,N-dimethylformamide (7 ml) was added sodium hydrogen carbonate (68 mg, 0.8 mmol) and 1-bromo-5-methylhexane (80 mg, 0.44 mmol). The stirred reaction mixture was heated to 100° C. for 16 h, then allowed to cool. Water (50 ml) was added and the mixture was extracted with diethyl ether (3*50 ml). The combined extracts were washed with brine (50 ml), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by silica (5 g) column chromatography eluding initially with hexane, then hexane:ethyl acetate:0.880 ammonia (50:50:1) to give a yellow oil (15 mg). The residue was further purified by preparative HPLC on a Phenomenex Magellan.(TM). column, 15 cm*2.1 cm; flow 10.0 ml min-1; employing U.V. detection at 235 nm; eluant acetonitrile:0.1M aqueous ammonium acetate solution:methanol (25:35:40) to afford the title compound as its acetate salt as a yellow oil (10 mg, 6percent). NMR (CDCl3, selected data for the acetate salt): 0.8 (d, 3H), 1.8 (m, 1H), 2.4 (m, 1H), 2.85 (m, 1H), 3.1 (q, 2H), 7.05-7.3 (m, 4H). MS (APCI): M/Z [MH+] 395.2; C22H38N2O2S+H requires 395.3.

The synthetic route of 1-Bromo-5-methylhexane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Armer, Richard Edward; Dutton, Christopher James; Gethin, David Morris; Gibson, Stephen Paul; Smith, Julian Duncan; Tommasini, Ivan; US2003/78282; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 5910-12-3, name is 3-Bromopyrazolo[1,5-a]pyridine, belongs to bromides-buliding-blocks compound, 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 5910-12-3, SDS of cas: 5910-12-3

Part B begins with commercially available bromo-pyrazolopyrimidine 47 (755 mg, 3.83 mmol) and 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-l,3)2-dioxaborolane (2.3 mL, 11.50 mmol) in THF (1.5 mL) at -78 0C. To this solution was added n-butyllithium (4.8 mL, 7.66 mmol) dropwise over 10 minutes. The reaction was slowly warmed to room temperature and was poured into water (10 mL) and partitioned with dichloromethane (10 mL). The organic was dried over sodium sulfate and concentrated before purification by column chromatography (0- 20% ethyl acetate in hexanes) to yield the boronic ester 48 (18% yield, 170 mg). 1H NMR (500 MHz, cdcl3) delta 8.54 – 8.44 (m, OH), 8.03 (s, 1 H), 7.65 (s, 1 H), 7.62 (d, J – 8.8, 1 H), 6.89 (d, J – 7.2, 1 H), 6.72 (x, J ‘ 54.4, 1 H), 6.20 (d, J = 9.3, 1 H), 4.37 – 4.06 (m, 1 H), 2.80 (t, J = 9.7, 1 H), 2.31 – 2.20 (m, IH), 2.10 (d, J = 13.7, IH), 1.92 – 1.73 (m, J = 26.0, 13.5, 2H), 1.44 – 1.16 (m, 2H).; Scheme 10.Stop A.Molecules of type 50 were prepared according to scheme 10 with the synthesis of compounds 46 and 48. Compound 46 (step A) was synthesized from commercially available dibromide 44. Regioselective metal-exchange followed by DMF quench provided aldehyde 46. Aldehyde 46 was reacted with excess deoxofluor to furnish compound 46. Preparation of boronic ester 48 (step B) was accomplished from commercial starting material (compound 47) via lithium-halogen exchange in the presence of 4,4,5>5-tetramethyl-2-(propan-2-yloxy)-l,3»2- dioxaborolane. Palladium-mediated coupling of 46 and 48 was followed by saponifcation to yield carboxylic acid 49. Amide formation with intermediate Il and subsequent deprotection provided compound 50.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromopyrazolo[1,5-a]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; KATZ, Jason; KNOWLES, Sandra, L.; JEWELL, James, P.; SLOMAN, David, L.; STANTON, Matthew, G.; NOUCTI, Njamkou; WO2010/17046; (2010); 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. 137-43-9, name is Cyclopentylbromide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C5H9Br

General procedure: Benzo[b]thiophene-3-carbaldehyde (40 mg, 0.25 mmol, 1.0 equiv),Pd(TFA) 2 (4.2 mg, 5 mol%), (4-FC 6 H 4 ) 3 P (9.5 mg, 12 mol%), DPEphos (8mg, 6 mol%), and Cs 2 CO 3 (122 mg, 0.375 mmol) were placed in atransparent Schlenk tube equipped with a stirring bar. The tube wasevacuated and filled with argon for three times. Degassed DMF (2.5mL) and tert-butyl bromide (51 mg, 0.375 mmol, 1.5 equiv) were add-ed via a gastight syringe. The reaction mixture was stirred under theirradiation of 36 W blue LEDs (distance app. 2.0-3.0 cm from thebulb) at r.t. for 24 h. The mixture was quenched with brine and ex-tracted with EtOAc (3 × 10 mL). The organic layers were combinedand concentrated under reduced pressure. The product was purifiedby flash column chromatography on silica gel using PE or a mixture of PEand EtOAc (10:1 v/v) as eluent; yield: 50.1 mg (92%); pale yellow liquid.

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 137-43-9.

Reference:
Article; Wang, Guang-Zu; Shang, Rui; Fu, Yao; Synthesis; vol. 50; 15; (2018); p. 2908 – 2914;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 73908-04-0, 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 73908-04-0 as follows.

General procedure: An oven-dried Schlenk tube containing a stirring bar was charged with NiI2 (2.5-10.0 mol%), L1 (4.4-17.6 mol%) and Mn powder (3 equiv.). The Schlenk tube was then evacuated and back-filled under a CO2 flow (this sequence was repeated three times) and finally an atmospheric pressure of CO2 was established. The corresponding alkyl bromide (0.5 mmol) and DMF (1 M) were added under a CO2 flow. Once added, the Schlenk tube was closed at atmospheric pressure of CO2 (1 atm) and stirred at the desired temperature for 20-48 h. The mixture was then carefully quenched with 2 M HCl to hydrolyse the resulting carboxylate and extracted with EtOAc (three times). The combined organic layer was washed with brine (three times), dried over anhydrous MgSO4, filtrated and evaporated. The resulting crude carboxylic acid was purified by conventional flash chromatography in silica gel using hexanes/EtOAc 3:1 with 1% formic acid.

According to the analysis of related databases, 73908-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Julia-Hernandez, Francisco; Moragas, Toni; Cornella, Josep; Martin, Ruben; Nature; vol. 545; 7652; (2017); p. 84 – 88;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 35354-37-1, 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 35354-37-1 as follows.

Example 148 (+-)-trans-3,4-Dimethyl-N-(5-methylhexyl)-4-(3-n-propanesulfonylaminophenyl)piperidine To a solution of (+-)-trans-3,4-dimethyl-4-(3-n-propanesulfonylaminophenyl)piperidine (Preparation 40, 220 mg, 0.71 mmol) and 1-bromo-5-methylhexane (140 mg, 0.78 mmol) in N,N-dimethylformamide (7 ml) was added sodium hydrogen carbonate (120 mg, 1.42 mmol) and the resultant mixture was heated overnight at 100° C. The reaction mixture was poured onto water (50 ml) and extracted with diethyl ether (3*50 ml). The combined extracts were washed with brine (50 ml), dried (MgSO4), filtered and concentrated in vacuo to give the crude product which was purified by silica (5 g) chromatography using a gradient solvent system eluding initially with hexane:0.880 ammonia (100:1) then ethyl acetate:hexane:0.880 ammonia (50:50:1) to afford the title compound as a pale yellow oil (77 mg, 27percent). NMR (CDCl3, selected data for the free base): 0.75 (d, 3H), 0.9 (d, 6H), 1.0 (t, 3H), 1.2 (t, 2H), 1.25 (m, 2H), 1.3 (s, 3H), 1.4-1.65 (m, 5H), 1.8 (m, 2H), 2.0 (m, 1H), 2.5 (q, 2H), 2.8 (m, 1H), 3.05 (m, 2H), 7.0-7.3 (m, 4H). MS (APCI): M/Z [MH+] 409.3; C23H40N2O2S+H requires 409.3.

According to the analysis of related databases, 35354-37-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Armer, Richard Edward; Dutton, Christopher James; Gethin, David Morris; Gibson, Stephen Paul; Smith, Julian Duncan; Tommasini, Ivan; US2003/78282; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 932-87-6, name is (Bromoethynyl)benzene, molecular formula is C8H5Br, 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. Computed Properties of C8H5Br

General procedure: A 5.0 mL of reaction tube was charged with organoboron compound (1.0 mmol), alkynyl bromide (1.0 mmol), CuI (0.10 mmol), 8-hydroxyquinoline (0.20 mmol), ethanol (2.0 mmol). The mixture was stirred at 80 C for 24 h, and then washed with ethyl acetate (3.0 mL×3), the combined ethyl acetate was concentrated under reduced pressure. The obtained residue was purified by flash column chromatography on silica gel (petroleum ether as eluting agent) to give the corresponding pure cross-coupling product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 932-87-6, its application will become more common.

Reference:
Article; Wang, Shihua; Wang, Min; Wang, Lei; Wang, Bo; Li, Pinhua; Yang, Jin; Tetrahedron; vol. 67; 26; (2011); p. 4800 – 4806;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1124-14-7, 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. 1124-14-7, name is 1-Bromo-4-cyclopropylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

Compound 45. A flask was flame dried under N2 blanket. Compound 44 (10.0 g, 50.7 mmol) was added, followed by dry THF (100 mL). The resulting solution was cooled to -78 C. A solution of n-butyl lithium in hexanes (2.27 M, 22.35 mL, 50.7 mmol) was added dropwise via syringe. The reaction mixture was stirred for 10 min. SO2 gas was bubbled into the reaction mixture until the pH of a reaction mixture sample was <1 when mixed with water. The reaction mixture was stirred for 30 min at -78 C. The ice bath was removed and the reaction mixture was allowed to warm to rt. The reaction mixture was stirred for an additional 30 min at rt. The reaction mixture was concentrated to afford a solid. CH2Cl2 (500 mL) and N-chlorosuccinamide (10.2 g, 76 mmol) were added and the reaction mixture was stirred for 4 hrs at rt. Water and CH2Cl2 were added and the layers were separated. The organic layer was washed with water and brine, then dried with MgSO4. The solution was filtered and the solvents were evaporated to give 13.3 g of crude p-cyclopropyl-benzenesulfonyl chloride (Compound 45). The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-cyclopropylbenzene. I believe this compound will play a more active role in future production and life. Reference:
Patent; Schering Corporation; US2003/232859; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 1159977-65-7, name is 6-Bromoimidazo[1,2-b]pyridazine, 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: 1159977-65-7

To a solution of 6-bromoimidazo[1,2-b]pyridazine (1.98 g, 10.0 mmol) in methanol (50 mL) at -10 C. was added N-iodosuccinimide (2.47 g, 11.0 mmol) in portions. The mixture was stirred at -10 C. for 30 minutes and then allowed to warm up to rt. The reaction was continued to stir at rt for 18 hours, and then concentrated in vacuo. The residue was dissolved in 100 mL of DCM and washed with 50 mL of aqueous Na2CO3 solution. The organic phase was concentrated in vacuo to give the title compound as a light yellow solid (2.0 g, 61%). MS (ESI, pos. ion) m/z: 323.9 [M+H]+; 1H NMR (400 MHz, CDCl3): delta 7.83 (s, 1H), 7.78 (d, J=9.4 Hz, 1H), 7.21 (d, J=9.4 Hz, 1H).

The synthetic route of 6-Bromoimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Calitor Sciences, LLC; Xi, Ning; US2014/134133; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 35354-37-1, 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. 35354-37-1, name is 1-Bromo-5-methylhexane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 151 (+-)-trans-3,4-Dimethyl-N-(5-methylhexyl)-4-(3-(1-methyl-1H-imidazole-4-sulfonylamino)phenyl)piperidine To a solution of (+-)-trans-3,4-dimethyl-4-(3-(1-methyl-1H-imidazole-4-sulfonylamino)phenyl)piperidine (Preparation 41, 80 mg, 0.23 mmol) in N,N-dimethylformamide (3 ml) was added sodium hydrogen carbonate (21 mg, 0.25 mmol) and 1-bromo-5-methylhexane (43 mg, 0.24 mmol). The stirred reaction mixture was heated at 100° C. for 5 h, then concentrated in vacuo at 80° C. The residue was taken up in dichloromethane and purified by silica column chromatography, eluding with ethyl acetate:isopropanol (95:5) to give the title compound as a white solid (34 mg, 33 NMR (CDCl3, selected data for the free base): 0.6 (d, 3H), 0.85 (m, 6H), 1.25 (s, 3H), 3.6 (s, 3H), 7.0-7.25 (s, 5H), 7.45 (s, 1H). MS (thermospray): M/Z [MH+] 447.3; C24H38N4O2S+H requires 447.3.

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-5-methylhexane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Armer, Richard Edward; Dutton, Christopher James; Gethin, David Morris; Gibson, Stephen Paul; Smith, Julian Duncan; Tommasini, Ivan; US2003/78282; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary