Tag: M.W=200-300

Synthetic Route of 104197-14-0, 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. 104197-14-0 name is 4-Bromo-2,6-difluoroanisole, 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.

[0241] Step a: Lithium diisopropylamine solution in THF (1 M, 25 mL, 25 mmol) was added slowly to a solution of 5-bromo-1,3-difluoro-2-methoxybenzene (4.5 g, 20.2 mmol) in anhydrous THF (50 mL) under N2 and vigorously stirred at 78 C. The reaction mixture was stirred at 60 C for 1 h, followed by rapid addition of DMF (5 mL). The reaction mixture was stirred at the same temperature and allowed to warm to 50 C over 1 h. The reaction was poured into a mixture of ice (200 g), concentrated hydrochloric acid (20 mL) and MTBE (100 mL) and the mixture was stirred and allowed to warm up to room temperature over 2 h. The oranic layer was separated, washed with brine and dried over MgSO4. The solvent was removed under reduced pressure to give 6-bromo-2,4-difluoro-3-methoxybenzaldehyde . MS: (ES) m/z calculated for C8H6BrF2O2 [M + H]+ 250.9, found 250.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroanisole, and friends who are interested can also refer to it.

Reference:
Patent; CHEMOCENTRYX, INC.; FAN, Pingchen; LANGE, Christopher W.; LUI, Rebecca M.; MALATHONG, Viengkham; MALI, Venkat Reddy; PUNNA, Sreenivas; SINGH, Rajinder; TANAKA, Hiroko; ZENG, Yibin; ZHANG, Penglie; (284 pag.)WO2018/222598; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 101-55-3, name is 1-Bromo-4-phenoxybenzene, belongs to ethers-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 101-55-3, Quality Control of 1-Bromo-4-phenoxybenzene

4-phenoxyphenylboronic acid (Intermediate V) To a solution of 4-phenoxybromobenzene (98.2 g, 0.39 mol) in dry THF (800 mL) under nitrogen at -78 C. was added n-BuLi (2.5M solution in hexanes) (172 mL, 0.43 mol) dropwise. A temperature rise to -65 C. was observed. On complete addition, the mixture was allowed to stir at -78 C. for 15 min. Triisopropylborate (109.2 mL, 0.473 mol) was added dropwise over 30 min. On complete addition, a suspension was observed. The mixture was allowed to warm to 0 C. over 1 hr, stirred at 0 C. for 4 hrs. The reaction was quenched by the dropwise addition of water (300 mL) such that the internal temperature <20 C. (ice-cooling required). The mixture was allowed to warm to room temperature overnight then evaporated to dryness. The residue was suspended in water (600 mL) and acidified by the cautious addition of conc. HCl. The resulting precipitate was collected by filtration and dried in vacuo at 45 C. The solid was ground to a fine powder and triturated with petroleum ether (40-60 C.). The pale solid was filtered and dried to give 4-phenoxyphenylboronic acid(68.8g, 83%). 1H NMR (250 MHz, d6-DMSO):7.99 (1H, m), 7.91 (1H, t), 7.83 (1H, d), 7.4 (2H, m), 7.14 (1H, m), 6.92-7.07 (5H, m). Microanalysis:Req. C(71.4%), H(5.45%), Found C(70.25%), 1H(4.7%) 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-4-phenoxybenzene, other downstream synthetic routes, hurry up and to see. Reference:
Patent; Abbott Laboratories; US2002/156081; (2002); A1;,
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Application of 91273-58-4, 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. 91273-58-4, name is ((3-Bromo-2-methylpropoxy)methyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 rac. E-1-benzyloxy-2-methyl-5-hepten-4-ol A slurry of 0.55 g. (0.0236 mole) of magnesium powder in 15 ml. of anhydrous tetrahydrofuran was stirred and heated at reflux while a few drops of a solution of 5 g. (0.0206 mole) of rac. 3-benzyloxy-2-methyl-1-propyl bromide in 30 ml. of anhydrous tetrahydrofuran was added followed by a crystal of iodine. After the Grignard reaction had begun, the remainder of the bromide solution was added dropwise over 35 min. at reflux temperature. The reaction mixture was stirred and heated under reflux for an additional hour then cooled 0-5 C. (ice bath) while a solution of 1.56 g. (0.022 mole) of crotonaldehyde in 15 ml. of anhydrous tetrahydrofuran was added over a 15 min. period. After stirring at room temperature for 2.5 hours, the reaction mixture was poured onto saturated aqueous ammonium chloride and the product was extracted with ether and worked up as in Example 1. The residue (4.62 g.) was chromatographed on 250 g. of silica gel. Elution with 4:1 parts by volume and 2:1 parts by volume hexane-ether gave 3.36 g. of rac. E-1-benzyloxy-2-methyl-5-hepten-4-ol as a pale yellow oil, b.p. 110-120 C. (bath temperature) (0.075 mm Hg.).

The synthetic route of ((3-Bromo-2-methylpropoxy)methyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US4041058; (1977); A;,
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Related Products of 36805-97-7,Some common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, molecular formula is C11H25NO2, 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.

Into the reaction vessel was added pyridine (50 mL) and dimethyl 4-hydroxyisophthalate (3.6 g, 17 mmol). The mixture was stirred at reflux for 17h andconcentrated. The residue was acidified with 1M HC1 (50 mL) and extracted with EtOAc (3OmL x 3). The organic phase was dried over Na2504, concentrated, and dissolved in DCM (10 mL). 1,1 -Di-tert-butoxy-N,N-dimethylmethanarnine (10.45 g, 51 .40 mmol) was then added and the reaction was stirred at rt for 12h. After diluted with EtOAc (30 mL), the organic phase was washed with sat NaHCO3 (20 mL x 3), dried over Na2SO4, andconcentrated to produce 1A (2.62 g, 10.40 mmol, 60.7% yield) as a white solid which was used for next step without further purification. LCMS Anal. Calc?d for C13H1605 252.10,found [M+H] 253.1; 1H NMR (500MHz, chloroform-d) 8 11.56 (s, 1H), 8.58-8.46 (m, 1H), 8.16 – 8.08 (m, 1H), 7.02 (s, 1H), 3.93 (s, 3H), 1.66 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SU, Shun; CHAO, Hannguang, J.; CLARKE, Adam, James; LAWRENCE, R., Michael; (169 pag.)WO2019/36024; (2019); A1;,
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Electric Literature of 588-96-5, The chemical industry reduces the impact on the environment during synthesis 588-96-5, name is p-Bromophenetole, I believe this compound will play a more active role in future production and life.

To a mixture of 1-bromo-4-ethoxybenzene (2 g, 9.95 mmol, 1.00 equiv) in THF (20 ml_) was added n-BuLi (2.5M in hexane, 3.98 ml_, 1.00 equiv) dropwise at -78C, the mixture was stirred at -78C for 30 min. 4-(Benzyloxy)-5-bromo-2-methylbenzaldehyde (3.025 g, 9.91 mmol, 1.00 equiv) in THF (10 ml_) was then added to the solution. The reaction mixture was stirred at -78C for 2h. NH4CI/H2O was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2SC>4. The mixture was concentrated and the resulting residue purified by chromatography on silica gel (3:1 PE/EA) to yield (4-(benzyloxy)-5-bromo-2-methylphenyl)(4-ethoxyphenyl)methanol as a yellow oil.

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, p-Bromophenetole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GUOZHANG, Xu; KUO, Gee-Hong; GAUL, Micheal; (163 pag.)WO2019/215633; (2019); A1;,
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Related Products of 588-96-5, 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. 588-96-5, name is p-Bromophenetole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Synthesis of (5-bromo-2-fluorophenyl)(4-ethoxyphenyl)methanol:To a stirred solution of Mg (9.5 g) in dry tetrahydrafuran (50 ml), 1-bromo- 4-ethoxybenzene (step 1, 53.4 g) in tetrahydrafuran (150 ml) was added under N2 atmosphere at room temperature slowly by drop wise and stirred for about 1 hour. Then 5-bromo-2-fluorobenzaldehyde (11 ml) was added slowly to the above reaction mixture and the reaction mixture was allowed to stir for over night. After completion of the reaction (monitored by TLC), the reaction mixture was poured into saturated NH4C1 solution at 0 C and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulphate and concentrated to give the residue. The crude product was purified via silica gel column chromatography with EtOAc and n-Hexane to afford the title compound as liquid (24 g). Yield: 85.7 ; NMR (CDC13, 300 MHz): delta 7.745- 7.71 (m, 1H), 7.37- 7.27 (m, 3H), 6.91- 6.84 (m, 3H), 6.02 (d, J = 3.3 Hz, 1H), 4.01 (q, J = 7.2 Hz, 2H), 2.20 (d, J = 3.3 Hz, 1H), 1.39 (t, J = 7.2 Hz, 3H).

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, p-Bromophenetole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HETERO RESEARCH FOUNDATION; PARTHASARADHI REDDY, Bandi; MANOHAR SHARMA, Vedula; RATHNAKAR REDDY, Kura; VL SUBRAHMANYAM, Lanka; SUDHAKAR, Neela; WO2012/25857; (2012); A1;,
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Synthetic Route of 106854-77-7, The chemical industry reduces the impact on the environment during synthesis 106854-77-7, name is 1-Bromo-4-(2,2,2-trifluoroethoxy)benzene, I believe this compound will play a more active role in future production and life.

Step 7: 1 -Benzyl-N,4-dimethyl-N-neopentyl-3-(4-(2,2,2-trifluoroethoxy)phenyl)-5- (trifluoromethyl)-1 H-pyrrole-2-carboxamide (SC-260)Under an nitrogen atmosphere 1 -benzyl-N,4-dimethyl-N-neopentyl-3-(4,4,5,5-tetramethyl-1 3,2- dioxaborolan-2-yl)-5-(trifluoromethyl)-1 H-pyrrole-2-carboxamide (106 mg, 0.216 mmol) was dissolved in DMF (1 mL) and L1OH (4 mg, 0.216 mmol), bis(tri-tert-butylphosphine)palladium (0) (6 mg, 0.014 mmol) and 1-bromo-4-(2,2,2-trifluoroethoxy)benzene (50 mg, 0.196 mmol) were subsequently added. The reaction mixture was stirred at 80C under microwave irridation for I h. The mixture was cooled to RT and the reaction was stopped by addition of 1 M NaOH solution (2 mL). The crude product was extracted with EtOAc (2×3 mL) and the combined organic layers were washed with water (3×1 mL), dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude mass was purified by flash chromatography to give SC-260 (95 mg, 89.7 %).

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-4-(2,2,2-trifluoroethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; STEINHAGEN, Henning; DAMANN, Nils; SKONE, Philip; HAMLYN, Richard; KIRBY, Robert; ROGERS, Marc; SUTTON, Kathy; WO2014/32801; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, belongs to ethers-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 1663-61-2, HPLC of Formula: C13H20O3

General procedure: The starting hydrazide 4, 8e-i (10 mmol) was added to a mixture of the appropriate triethyl orthoester (10 mol) and 0.1 g p-TsOH in 20 mL of xylene and kept under reflux for 3 h (TLC). After cooling, the mixture was washed with water (30 mL), dried over MgSO4 and then concentrated under reduced pressure. The oily residue was subjected to column chromatography (silica gel, eluent: hexane/AcOEt, 1:2 v/v) or crystallised from benzene/hexane mixture.

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, (Triethoxymethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Ejsmont, Krzysztof; Tetrahedron; vol. 67; 40; (2011); p. 7838 – 7845;,
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These common heterocyclic compound, 7025-06-1, name is 1-Bromo-2-phenoxybenzene, 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: 1-Bromo-2-phenoxybenzene

30 g of 1-bromo-2-phenoxybenzene was dissolved in 300 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere,-78 ¡ã CRespectively.to the next,48 ml of 2.5 M-butyllithium was slowly added dropwise.After completion of the dropwise addition, stirring was performed for 30 minutes,2-Bromofluorene 31.2 gWas dissolved in 200 ml of absolute tetrahydrofuran and then slowly added dropwise.The reaction solution was maintained at -78 ¡ã C for about 1 hour, then warmed to room temperature and stirred for 12 hours.The reaction was terminated by adding diluted hydrochloric acid to the reaction solution, followed by liquid fraction extraction using methylene chloride.The obtained organic layer was dried with magnesium sulfate, filtered, and then distilled under reduced pressure. to the next,After adding 400 ml of acetic acid, a catalytic amount of hydrochloric acid was added dropwise, followed by stirring at a reflux temperature for 12 hours.After completion of the reaction, the reaction mixture was cooled to obtain a solid,After filtration, 32.0 g of compound AA was obtained by column chromatography.

The synthetic route of 1-Bromo-2-phenoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG CHEM, LTD.; HONG, WAN PYO; KWON, HYOK JOON; KIM, KONG KYEOM; KIM, MIN JUN; KIM, SEONG SO; (79 pag.)KR2017/59910; (2017); A;,
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Synthetic Route of 13940-96-0, The chemical industry reduces the impact on the environment during synthesis 13940-96-0, name is 4-Phenoxybenzene-1,2-diamine, I believe this compound will play a more active role in future production and life.

In a 1000 ml flask equipped with a stirring blade and a reflux condenser, 750 g of a methyl t-butyl ether solution containing 12% by mass of 3,4-diaminodiphenyl ether and 150.8 g (1.13 mol) of acetic anhydride were charged, The reaction was carried out for 2 hours under heating reflux. From the reaction solution, about 500 g of methyl t-butyl ether was distilled off under reduced pressure to obtain a concentrated solution. The obtained concentrated liquid was poured into 1,000 g of a 20% sodium hydroxide aqueous solution to precipitate an N, N-diacetylated product of 3,4-diaminodiphenyl ether to obtain a solid-liquid mixture.

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-Phenoxybenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JFE CHEMICAL CORPORATION; MORI, HIROAKI; (9 pag.)JP2016/6020; (2016); A;,
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