Author: Jessica.F

Some common heterocyclic compound, 156682-52-9, name is 1,4-Dibromo-2,3-difluorobenzene, molecular formula is C6H2Br2F2, 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. HPLC of Formula: C6H2Br2F2

Preparation of iso-PrMgCl-LiCl-A sample of LiCl (4.56 g, 107.6 mmol) was dried under high vacuum with a heat gun for 10 min. To the dry solid under a N2 atmosphere at 23 C. was added iso-PrMgCl (53.8 mL, 107.6 mmol, 2M solution in THF) and the resulting mixture was stirred at 23 C. for 3 days.To a solution of D-1c (1.29 mL, 10 mmol) in THF (5 mL) at 40 C. was added the iso-PrMgCl-LiCl solution (5.5 mL, 11 mmol, 2.0M in THF) at a rate that maintained the reaction temperature below -30 C. Stirring was continued at -35 to -30 C. for 1 h then warmed to -7 C. for an additional 1 h. The reaction mixture was cooled to -30 C. and DMF (1.00 mL, 13 mmol) was added in one portion (temperature rose to -23 C.) and stirring continued for 3.5 h at -25 to +15 C. The reaction mixture was poured into 1M H2SO4 and ice and the resulting mixture was saturated with solid NaCl and twice extracted with MTBE. The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford 2.17 g (98%) of D-1d as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 156682-52-9, its application will become more common.

Reference:
Patent; Roche Palo Alto LLC; US2008/249151; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 39478-78-9, name is 5-Bromo-2-methylaniline, 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 39478-78-9, Computed Properties of C7H8BrN

General procedure: Under N2 atmosphere, a mixture of 6 (100.0 mg, 0.26 mmol),Pd(pph3)4 (30.0 mg, 0.026 mmol), 2.0M aq Na2CO3 (0.29 ml,0.78 mmol) and 1-Methyl-1H-pyrazole-5-boronic acid pinacolester (108.2 mg, 0.52 mmol) in 1,4-Dioxane (0.65 ml) was heated to90 C and stirred for 6 h. The reaction mixture was cooled, dilutedwith ethyl acetate, washed with water, dried over anhydrousNa2SO4, filtered and concentrated under vacuum. Purification onsilica using a solvent gradient of 10-30% ethyl acetate in hexanesyielded the desired compound 1j (77.0 mg, 77.5%). Compounds 1akwere prepared according to general procedure as described forcompound 1j using corresponding aryl bromide 2-4 and theappropriate boronic acid or boronic acid pinacol ester. The characterizationdata for compounds 1a-k were provided below.

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, 5-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Yu, Jiang; Zhang, Lanxi; Yan, Guoyi; Zhou, Peiting; Cao, Chaoguo; Zhou, Fei; Li, Xinghai; Chen, Yuanwei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 265 – 281;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 15155-41-6, A common heterocyclic compound, 15155-41-6, name is 4,7-Dibromo-2,1,3-benzothiadiazole, molecular formula is C6H2Br2N2S, 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.

In two 250mL flask, followed by adding ethanol 150ml, 2,5- dibromo benzothiadiazole (5. 88g, 20mmol), the flask was placed in an ice-water bath, sodium borohydride was slowly added repeatedly (1. 52g, 40mmol after), 0 C reaction lOmin, room temperature, the reaction 3h, the reaction was completed. After rotary evaporation to dryness in vacuo purified by column chromatography, petroleum ether: dichloromethane = 1: 1 to giveOff-white product 5. 05g (95% yield).

The synthetic route of 15155-41-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NanjingFriend Photoelectric Technology Co., Ltd; MENG, HONG; ZHANG, XIAOTAO; YUAN, XIAO; YAN, LIJIA; (10 pag.)CN103450226; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 615-55-4, name is 3,4-Dibromoaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H5Br2N

EXAMPLE 20 4-[(3,4-Dibromophenyl)amino]-6-nitro-3-quinolinecarbonitrile A mixture of 6.20 g (26.6 mmol)of 4-chloro-6-nitro-3-quinolinecarbonitrile and 8.00 g (31.9 mmol) of 3,4-dibromoaniline in 160 mL of ethanol was refluxed under N2 for 5 h. Saturated sodium bicarbonate was added and volatile material was removed. The residue was slurried with hexane, collected, washed with hexane and water and dried. The insoluble material was repeatedly extracted with boiling ethyl acetate and the solution was then filtered through silica gel. The solvent was removed to give 3.80 g of green solid: mass spectrum (electrospray, m/e): M+H 449.

The synthetic route of 615-55-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6002008; (1999); A;; ; Patent; American Cyanamid Company; US6384051; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 10269-01-9, name is (3-Bromophenyl)methanamine, 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

General procedure: A mixture of 1,3-dione (1.5 mmol) and benzylamine (1.5 mmol) was stirred in refluxing EtOH (78 C) for 2 hrs under air. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to 10 C. Crystalline solid was filtere out. No further purification was needed.

The synthetic route of (3-Bromophenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sarkar, Rajib; Mukhopadhyay, Chhanda; Tetrahedron Letters; vol. 59; 32; (2018); p. 3069 – 3076;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 3814-30-0, 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.

A solution of diethyl malonate (36.91 g, 230.4 mmol), anhydrous methanol (400 mL), and NaOMe (25% in methanol, 49.79 g, 230.4 mmol) is stirred at reflux for one hour under nitrogen. Bromomethyl-cyclopentane (31.31 g, 192.0 mmol) is added to the mixture, and stirred for an additional 3 hours. A solution of NaOH (23.04 g, 576.0 mmol) in water (400 mL) is added, and the mixture is stirred for an additional 1 hour at reflux. The mixture is cooled, diluted with water, and extracted with ether. The ether layer is discarded, and the aqueous layer is acidified with 1N HCI to pH=1. The aqueous layer is extracted with EtOAc. The EtOAc layers are combined, dried over Na2SO4, and concentrated. This gives 2- cyclopentylmethyl-malonic acid (21.0 g, 59% yield) as a white solid.

Statistics shows that (Bromomethyl)cyclopentane is playing an increasingly important role. we look forward to future research findings about 3814-30-0.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GmbH; VICURON PHARMACEUTICALS, INC; WO2006/127576; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 142808-15-9, 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. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00199] step 2: (R)-tert-butyl 2-(3 -fluoro-4-(trifluoromethyl)benzoyl)pyrrolidine- 1 -carboxylate. To a stirred solution of 4-bromo-2-fluoro-l-(trifluoromethyl)benzene (4.854 g, 19.98 mmol) and ether (50 mL) cooled to -78 C under nitrogen was added w-butyl lithium (7.99 mL, 19.98 mmol) slowly over 10 min. The reaction was transferred via cannula to a solution of 42b (4.30 g, 16.65 mmol) in THF (50 mL) cooled to -78 C. The reaction was stirred for 10 min after all aryl lithium was added. The reaction was quenched with water and extracted with DCM. The organic layer was dried (MgS04), concentrated and the crude product purified by Si02 chromatography eluting with an EtOAc/hexane gradient (1 to 5% EtOAc). A close running impurity was not removed by this purification. The compound was further purified on a SP4 reverse phase column chromatography eluting with MeCN/water gradient (65 to 100% MeCN) to afford 2.105 g (33.2%) of 44.

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, 4-Bromo-2-fluorobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; BLAKE, James, F.; CHEN, Huifen; CHICARELLI, Mark, Joseph; DEMEESE, Jason; GARREY, Rustam, Ferdinand; GAUDINO, John; GAZZARD, Lewis; KAUS, Robert J.; KINTZ, Samuel; MOHR, Peter J.; MORENO, David, A.; SCHWARZ, Jacob; SIEDEM, Christopher, S.; WALLACE, Eli, M.; WO2013/20062; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 615-54-3, The chemical industry reduces the impact on the environment during synthesis 615-54-3, name is 1,2,4-Tribromobenzene, I believe this compound will play a more active role in future production and life.

Step 1: Into a 100-nt 3-necked round-bottom flask, was placed a mixture of 1,2.4- tribromobenzene (5,20 g, 16.52 mmol, 1.00 equiv) and 2-methylfuran (4.18 g. 50.91 mmol,3.00 equiv) in toluene (30 mL) with stirring at -30 C, followed by the drop-wise addition of n-BuLi (7.48 mL, 1.10 equiv). The resulting mixture was stirred for 30 mm at -30 C then it was quenched by the addition of 50 mL of 1120, cooled to RT and extracted with 3 x 50 mL of ethyl acetate. The organic layer was washed with 200 mL of 1120, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gelcolumn chromatography eluting with ethyl acetate/petroleum ether (1:3) to deliver 2.10 g (54%) of a mixture of (+)-4-bromo- i-methyl-li -oxatricyclo [6.2.1. 02?7jundeca-2,4,6,9- tetraene and (+)-5-bromo- i-methyl-il -oxatricyclo[6. 2.1.0271 undeca-2,4,6,9-tetraene as a light yellow solid. Step 2: Into a l00-mL 3-necked round-bottom flask, was placed a solution of (+)-4- bromo- 1-methyl-il -oxatricyclo [6.2.1.0271 undeca-2,4,6,9-tetraene and (+)-5-bromo- 1-methyl- l1-oxatricyclo[6.2.1.02?7jundeca-2,4,6,9-tetraene (2.10 g, 8.86 mmol, 1.00 equiv) in chloroform (30 mL) with stirring at rt, followed by the slow addition of a solution ofbis(pyridin-2-yl)-1,2,4,5-tetrazine (2.40 g, 10.16 mmol, 1.10 equiv) in chloroform (20 mL). The resulting mixture was stirred for 1 h at 50 C to deliver the mixture of corresponding isobenzofurans intermediate (50 mL) as a red solution. To this solution into a 100-mL 3- necked round-bottom flask at 0 C was added a solution of [5-(methoxycarbonyl)-2- (trimethylsilyl)phenyl](phenyl)iodanium trifluoromethanesulfonate (5.60 g, 9.99 mmol, 1.00equiv) in dichioromethane (40 mL), followed by TBAF (5.23 g, 20.00 mmol, 2.00 equiv). The resulting mixture was stirred for 30 mm at 0 C then it was concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:3) to deliver 900 mg (26%) of (+)-methyl 12-bromo-8-methyl-15- oxatetracyclo [6,6,1,027, 4i pentadeca-2(7),3 ,5,9, 11,13 -hexaene-4-carboxylate, (+)-methyl11 -bromo-8-methyl- 1 5-oxatetracyclo[6. 6.1. 02?.O9?14jpentadeca-2(7),3,5,9,1 1,1 3-hexaene-4- carboxylate, (+)-methyl 1 2-bromo- 1-methyl-i 5-oxatetracyclo-[6. 6,i,02?. 09?14jpentadeca- 2(7),3,5,9. 11,1 3-hexaene-4-carboxylate and (+)-methyl ii -bromo- i-methyl-i 5- oxatetracyclo [6.6. i .027. 14j pentadeca-2(7),3 ,5 ,9, ii, i 3 -hexaene-4-carboxylate as a light yellow solid. Step 3: Into a 50-mL round-bottom flask, was placed a mixture of (+)-methyl i2- bromo-8-methyl-1 5-oxatetracyclo[6. 6.1.02,7. 09?4jpentadeca-2(7),3,5,9, ii, i 3-hexaene-4- carboxylate (+)-methyl ii -bromo-8-methyl- i 5-oxatetracyclo[6. 6. i .02,7. ue 14j pentadeca2(7),3,5 ,9. 11,1 3-hexaene-4-carboxylate, (+)-methyl 1 2-bromo- 1-methyl- 15- oxatetracyclo[6.6. 1.027.09141 -pentadeca-2(7),3.5.9,1 1, i 3-hexaene-4-carboxylate and (+)-methyl ii -bromo- i-methyl-i 5-oxatetracyclo[6. 6. i .02,7. 09?4jpentadeca-2(7),3,5,9, ii ,13- hexaene-4-carboxylate (500.0 mg, 1.45 mmol, 1.00 equiv), dioxane/H20 (5/0.5 mL), (4- fluorophenyl)boronic acid (665.0 mg, 4.75 mmol, 1.50 equiv), sodium carbonate (46i.0 mg, 4.35 mmol, 3.00 equiv) and Pd(dppf)Cl2 (53.0 mg, 0.07 mmol, 0.05 equiv) with stirring under N2. The resulting mixture was stirred for 3 h at 90 C then it was cooled to RT andconcentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (iS) to afford 4 i 0.0 mg (79%) of a mixture of (+)-methyl 1 2-(4-fluorophenyl)-8-methyl- i 5-oxatetracyclo- [6.6. i .02,7. ?4jpentadeca- 2(7),3,5 ,9. ii, 1 3-hexaene-4-carboxylate, (+)-methyl ii -(4-fluorophenyl)-8-methyl- 15-oxatetracyclo [6.6.1.02,7. ue 14j pentadeca-2(7),3 ,5,9, 11,13 -hexaene-4-carboxylate, (+)-methyl 12-(4-fluorophenyl)-1 -methyl-i 5-oxatetracyclo[6. 6.1. 02?7.09?4j-pentadeca-2(7),3,5,9, 11,13- hexaene-4-carboxylate and (+)-methyl ii -(4-fluorophenyl)- 1-methyl-i 5- oxatetracyclo [6.6.1.027. 14j pentadeca-2(7),3 ,5 ,9, 11,13 -hexaene-4-carboxylate as a lightyellow solid..

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, 1,2,4-Tribromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; LI, Zhe; ZANCANELLA, Manuel; YU, Chul; SETTI, Lina; SHAM, Hing; XU, Qing; YEE, Calvin; YU, Ming; (402 pag.)WO2016/201052; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 17247-58-4, name is (Bromomethyl)cyclobutane, 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 17247-58-4, Product Details of 17247-58-4

To a stirred solution of 14 (100 mg, 0.32 mmol) in DMF (1 mL) were added K2CO3 (310 mg, 2.22 mmol) and (bromomethyl)cyclobutane (150 muL, 1.27 mmol), and stirred at 60 C under an Ar atmosphere. After 24 h with stirring, the reaction mixture was evaporated in vacuo. The resulting mixture was basified (pH 9) with saturated NaHCO3 aqueous solution and extracted with CHCl3 three times. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by preparative TLC (CHCl3/MeOH = 10/1) to give 17 (79 mg, 65%) as a colorless oil. IR (neat): 2936, 1611, 1497 cm-1; 1H NMR (CDCl3, 400 MHz) delta: 1.30-1.38 (1H, m), 1.40-1.53 (2H, m), 1.57 (1H, d, J = 14.4 Hz), 1.60-1.92 (8H, m), 1.93-2.12 (3H, m), 2.40-2.62 (5H, m), 2.63 (1H, dd, J = 6.4, 18.0 Hz), 2.92-2.98 (1H, m), 2.94 (1H, d, J = 18.0 Hz), 3.72-3.79 (1H, m), 3.76 (3H, s), 3.80-3.86 (2H, m), 3.89-3.96 (1H, m), 6.68 (1H, dd, J = 2.8, 8.4 Hz), 6.81 (1H, d, J = 2.8 Hz), 6.98 (1H, d, J = 8.4 Hz). MS (ESI) m/z = 384 [M+H]+. HRMS (ESI) Calcd for C24H34NO3 [M+H]+: 384.2539. Found 384.2548.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Ida, Yoshihiro; Nemoto, Toru; Hirayama, Shigeto; Fujii, Hideaki; Osa, Yumiko; Imai, Masayuki; Nakamura, Takashi; Kanemasa, Toshiyuki; Kato, Akira; Nagase, Hiroshi; Bioorganic and Medicinal Chemistry; vol. 20; 2; (2012); p. 949 – 961;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1435-53-6,Some common heterocyclic compound, 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene, molecular formula is C6H3Br2F, 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 10b (0873) 28.5 g (0.1 12 mol) 1 ,3-dibromo-4-fluorobezene, 23.5 g (0.1 12 mol) N-phenyl-1 H-benzimidazol- 2-amine and 59.6 g (0.281 mol) potassium phosphate tribasic in 250 ml DMA were stirred at 160 C for 20 h under nitrogen. The reaction mixture was poured on water. The product was filtered off washed with water and ethanol. (0874) Yield 38.9 g (97.6 %). (0875) 1H NMR (400 M Hz, CDCI3): delta =7.78-7.83 (m, 4H), 7.64-7.70 (m, 4H), 7.48-7.52 (m, 2 H), 7.40 (dt, 1 H), 7.33 (dt, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dibromo-1-fluorobenzene, its application will become more common.

Reference:
Patent; IDEMITSU KOSAN CO., LTD.; SCHAeFER, Thomas; FLORES, Jean-Charles; NAGASHIMA, Hideaki; (236 pag.)WO2017/93958; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary