Tag: M.W=100-200

Synthetic Route of 103-64-0, 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. 103-64-0, name is (2-Bromovinyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation of trans- beta -styrenyl-phenylsulfide [formula 8] A solution of palladium acetate (4.5 mg, 0.02 mmol) and Xantphos (12.7 mg, 0.022 mmol) in DMF (1 niL) was stirred for 5 minutes under a nitrogen atmosphere. To this solution was added 1-bromostyrene (91.5 mg, 0.5 mmol) dissolved in 0.5 mL of DMF and then the reaction mixture was stirred for 10 minutes at room temperature. Li(SPh)3 (74mg, 0.167 mmol) in DMF ( 1 mL) and diisopropylethyl amine (65 mg, 0.5 mmol) were added to this reaction mixture.The reaction mixture was stirred for 2 hours at 100 degrees Celsius. The solution was cooled to room temperature and then 1 mL of hydrochloric acid (5 % of aqueous solution) was added to stop the reaction. The crude product was extracted with diethyl ether (15 mL, 3 times) and sequentially washed with 10 mL of water, a saturated NaHCO3 (10 mL) solution and a saturated NaCl (20 mL) solution. The extracted organic compound was dried over anhydrous MgSO4 and then filtered. After evaporation of solvents, the crude product was purified by column chromatography to give /r°«s-beta-styrenyl-phenylsulfide (101 mg, 95 %) (formula 8). 1H-NMR (300 MHz, CDCl3) delta 7.60(m, 10H), 6.70(d, J=15.4Hz, IH), 6.62(d, J=15.4Hz, IH).

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-Bromovinyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KNU-INDUSTRY COOPERATION FOUNDATION; WO2009/69888; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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 2270-59-9 as follows. COA of Formula: C6H11Br

Example 5: Synthesis of N-[(l a, 5 a, 6 aV3-(4-methvl-pent-3-enyl)-3-aza-bicyclor3.1.01hex-6-vlmethyl)-9H-xanthene-9-carboxylic acid amide (Compound No. 8); To a solution of the compound No. 2 (1 mmol) in acetonitrile (5.0 ml), was added 5-bromo-2-methyl-pent-2-ene (1.2 mmol), potassium carbonate (8 mmol) and potassium iodide (2 mmol). The reaction mixture was refiuxed for overnight. The reaction mixture was concentrated under reduced pressure and the residue thus obtained was taken in water ;and extracted with ethyl acetate. The organic layer was dried over anhydrous sodiumsulphate and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by column chromatography using ethylacetate in hexane as eluent to furnish the title compound (80%).IR(KBr): 1639.9 cm-1lR NMR (CDC13):8 7.28-7.40 (m, 4H), 7.10-7.15 (m, 4H), 5.50 (brs, 1H), 5.00 (m, 1H), 4.87 (s, 1H), 3.03-3.07 (m, 2H), 2.64-2.66 (m, 4H), 2.33 (m, 2H), 1.68 (s, 3H), 1.62 (s, 3H), 1.33-1.37 (m, 2H), 0.86-0.88 (m, 1H).Mass (m/z): 403 (M++l).

According to the analysis of related databases, 2270-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2006/5980; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 6911-87-1,Some common heterocyclic compound, 6911-87-1, name is 4-Bromo-N-methylaniline, molecular formula is C7H8BrN, 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.

[00347] Step 1. To a stirred solution of 4-bromophenyl methyl amine 63-A (0.098 mL, 0.78 mmol) in 5 mL of CH2CI2 was added triethyl amine (0.217 mL, 1.55 mmol) followed by 2- chloro-6-fluoro-benzoyl chloride 1-B (0.116 mL, 0.881 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, and then washed with a sat. NaHC03 aqueous solution, H20, and brine. The organic layer was dried over anhydrous Na2S04. Solvents were removed in vacuo, the residue was purified by gradient column chromatography eluting with EtOAc / Heptanes to give the amide intermediate 63-B (270 mg, 100%). LC-MS: m/z = 341.9 [M+H]+.

The synthetic route of 6911-87-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC.; CHAO, Jianhua; ENYEDY, Istvan, J.; GUERTIN, Kevin; HUTCHINGS, Richard, H.; JONES, John, Howard; POWELL, Noel; VANVLOTEN, Kurt, D.; WO2014/8214; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 2695-48-9, A common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, molecular formula is C8H15Br, 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.

A suspension of Mg (30.6 mg, 1.26 mmol) and 8-bromo-1-octene (0.20 mL, 1.19 mmol) in THF (10 mL) was stirredat 50C. After being stirred for 1 h, Mg solid was perfectlyconsumed. To a solution of 9 (0.11 mL, 1.00 mmol) and NiCl2(16.3 mg, 0.0300 mmol) in THF (5.0 mL) was added the prepared7-octenylmagnesium bromide at 0C and the mixturewas stirred at room temperature for 1 h. After the additionof sat. NH4Cl aq. (30 mL) at 0C, the reaction mixture wasextracted with EtOAc (10 mL × 3), dried over MgSO4, andconcentrated under reduced pressure. The residue was purifiedby silica gel column chromatography (hexane-EtOAc = 5 : 1)to afford 7 (67.6 mg, 0.290 mmol, 29%) as a colorless oil.

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:
Article; Kutsumura, Noriki; Inagaki, Mai; Kiriseko, Akito; Saito, Takao; Chemical and Pharmaceutical Bulletin; vol. 67; 6; (2019); p. 594 – 598;,
Bromide – Wikipedia,
bromide – Wiktionary

114078-88-5, name is 5-Bromo-1,2,3-triazine, 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. Quality Control of 5-Bromo-1,2,3-triazine

To a solution of 5-bromotriazine (20.0 g, crude) in 1,4-dioxane (600 mL) was added pyrimidine-2-carboxamidine (16.8 g, 137.53 mmol) at 0 C. After being stirred at 0 C for 1 hrs, the resulting mixture was warmed to 30 C and stirred at 30 C for 1 hr, and then filtered. The filtrate was concentrated in vacuo. The residue was diluted with H20 (500 mL) and extracted with DCM (500 mL) for three times. The combined organic layer was washed with brine (1.0 L), dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified on silica gel column (eluting with DCM/MeOH= 10/1, v:v) to give 5-bromo-2-pyrimidin-2-yl-pyrimidine (9.0 g) as yellow solid.

The synthetic route of 114078-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Jianhua; WANG, Min; YANG, Song; (81 pag.)WO2018/83136; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1422-54-4,Some common heterocyclic compound, 1422-54-4, name is 2-Bromo-6-fluorotoluene, molecular formula is C7H6BrF, 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 187 6-(3-Fluoro-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 287, structure 4 of Scheme II, where R1 =3-fluoro-2-methylphenyl) This compound was prepared by General Method 2 (EXAMPLE 9) from Compound 9 (50 mg, 0.158 mmol) and 2-bromo-6-fluorotoluene (60 mg, 0.315 mmol). Purification by flash chromatography on silica gel (20 g) using 5% EtOAc:hexanes afforded 6 mg (14%) of Compound 287 as a yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-6-fluorotoluene, its application will become more common.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696130; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 103-64-0, name is (2-Bromovinyl)benzene, 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 103-64-0, Quality Control of (2-Bromovinyl)benzene

beta-Bromostyrene (7 mL, 54.57 mmol) was dissolved in 64 mL Et2O and cooled to -78 C. t-BuLi (1.6M in pentane, 64 mL, 102.4 mmol) was added over 40 min. The mixture was stirred at -78 C for 1 h, at which time (R)-7-allyl-3-isobutoxy-7-methylcyclohept-2-enone (4, 7.8335 g, 33.14 mmol) in 15 mL Et2O was added by cannula with a 5 mL rinse. After 90 min, the reaction was warmed with an ice bath and stirred for 1 h. The reaction was quenched with 10% HCl (100 mL), and the volatiles removed in vacuo. To the residue was added 100mL THF. The mixture was then heated to 50 C for 12 h. After cooling to room temperature, the mixture was extracted 4 * 100mL Et2O. The combined organic extracts were dried over MgSO4, and evaporated in vacuo. Silica gel chromatography (5 * 17 cm, ~700 mL 20:1 hexanes:EtOAc then~1.6 L 15:1 hexanes:EtOAc) afforded the title compound as a viscous yellow oil (8.0542 g, 91% yield). RF = 0.23 (10:1 Hexane:EtOAc); 1H NMR (300 MHz, CDCl3) delta 7.45-7.27 (m, 5H), 6.90 (s, 2H), 6.31 (s, 1H), 5.68 (dddd, J = 6.6, 8.1, 10.5, 17.1 Hz, 1H), 5.09-5.01 (m, 2H), 2.66-2.61 (m, 2H), 2.47 (dd, J = 6.6, 14.1 Hz, 1H), 2.14 (dd, J 8.1,14.1 Hz, 1H), 1.93-1.80 (m, 3H), 1.70-1.60 (m, 1H), 1.27 (s, 3H); 13C NMR (125 MHz, CDCl3) delta 204.5, 158.3, 136.5, 133.7, 133.1, 129.0, 128.7, 128.3, 126.9, 126.9, 118.3, 46.0, 44.3, 44.2, 38.5, 26.6, 17.4; IR (Neat Film NaCl) 3075, 3026, 2925, 1640, 1582, 1450, 1344, 1250,1217, 963, 916, 752, 694 cm-1; HRMS m/z calc’d for C19H22O [M]+: 266.1671, found 266.1668; [alpha]D24.8 +33.70 (c 1.19, CHCl3, 88% ee).

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

Reference:
Article; Harned, Andrew M.; Stoltz, Brian M.; Tetrahedron; vol. 75; 24; (2019); p. 3166 – 3177;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 766-46-1, 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. 766-46-1, name is 2′-Bromophenylacetylene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a 25 mL of flask, t-BuLi (2 mmol, 1.6 M in pentane) was added dropwise at -78 C to a stirred solution of o-bromoethynylbenzene (1 mmol, 181 mg) or its derivative (1 mmol) in Et2O (5 mL) and the reaction mixture was allowed to warm to room temperature. After stirring at room temperature for 1 h, S8 (0.25 mmol, 64 mg) was added and the reaction was stirred at room temperature for 2 h. The solvent of the reaction mixture was evaporated under vacuum and THF (5 ml) was added. After that, an electrophile (2 mmol) was added dropwise at room temperature. After stirring at room temperature for 1 h, the solvent of the reaction mixture was evaporated under vacuum. The residue was purified by chromatography to give products 4 and 6.

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

Reference:
Article; Wang, Zitao; Geng, Weizhi; Wang, Hanliu; Zhang, Shaoguang; Zhang, Wen-Xiong; Xi, Zhenfeng; Tetrahedron Letters; vol. 52; 51; (2011); p. 6997 – 6999;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 348-57-2, A common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, molecular formula is C6H3BrF2, 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 solution of 1-bromo-2,4-difluorobenzene (1.65 g, 8.57 mmol) in diethyl ether (Et2O; 10 mL) were added sequentially n-butyllithium (n-BuLi, 2.3 Molar (M) in hexane; 3.70 mL, 8.57 mmol) at -70° C. and the above ester (2.40 g, 8.57 mmol) in Et2O (5 mL) after 15 minutes (min). The reaction mixture was stirred for 1 h at -70° C., warmed to RT and stirred for another 2 h. The reaction mixture was quenched with aq NH4Cl solution and extracted with EtOAc (3.x.20 mL). The combined organic layers were washed with H2O, washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude compound was purified by column chromatography (eluting with EtOAc/hexane) to afford ketone B (1.30 g, 3.73 mmol, 43percent) as a yellow liquid. 1H NMR (500 MHz, CDCl3): 88.62 (s, 1H), 8.08-8.04 (m, 2H), 7.74-7.70 (m, 1H), 7.05-6.95 (m, 1H), 6.88-6.78 (m, 1H). MS (ESI): m/z 347, 349 [(M++1)+2].

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; Viamet Pharmaceuticals, Inc.; US2012/329788; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2550-36-9, These common heterocyclic compound, 2550-36-9, name is (Bromomethyl)cyclohexane, 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.

A suspension of compound 33 (496 mg, 2.88 mmol), solid potassium hydroxide (182 mg, 3.24 mmol) and tetrabutyl ammonium bisulfate (11 mg, 0.29 mmol) in toluene (4 mL) was heated to 50 C and the reaction was conducted for 2 h with vigorous stirring. To the above reaction mixture bromomethyl cyclohexane (639 mg, 3.61 mmol) was added dropwise and the reaction mixture was heated to 80 C. After 2 h, the reaction was cooled to rt, diluted with ethyl acetate, washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated to yield the product 34 as a yellow oil which is a mixture of rotamers (720 mg, 2.68 mmol, 93%); 1H NMR (CDCl3) delta 0.84-1.07 (m, 2H), 1.08-1.32 (m, 4H), 1.44 and 1.50 (s, 9H), 1.57-1.77 (m, 5H), 1.80 and 1.86 (s, 3H), 2.03 and 2.06 (s, 3H), 3.31 (d, J = 8.00 Hz, 2H).

Statistics shows that (Bromomethyl)cyclohexane is playing an increasingly important role. we look forward to future research findings about 2550-36-9.

Reference:
Article; Purohit, Meena K.; Chakka, Sai Kumar; Scovell, Iain; Neschadim, Anton; Bello, Angelica M.; Salum, Norue; Katsman, Yulia; Bareau, Madeleine C.; Branch, Donald R.; Kotra, Lakshmi P.; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2739 – 2752;,
Bromide – Wikipedia,
bromide – Wiktionary