Category: chlorides-buliding-blocks

Some common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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. Product Details of 6940-78-9

The solution of isobutyronitrile (0.7 g, 10 mmol) in THF (20 mL) was cooled to -80 C and LDA (Lithium diisopropylamide) solution (2.0 M in hexane, 6 mL, 12 mmol) was added over 10 min. The solution was stirred 30 min, and then a solution of 1-bromo-5-chloropentane (1.8 g, 10 mmol) in THF (10 mL) was added over 5 min. After stirring for 90 min, 6 N HCl (6 mL) was added slowly and the temperature allowed to rise to rt. The residue was concentrated under reduced pressure and EtOAc (20 mL) was added. The separated organic layer was washed with water (10 mL). The organic solvent was dried with Na2SO4 and concentrated in vacuo to give the crude product. Purification by column chromatography (petroleum ether (60-90 C)/EtOAc) gave 1.5 g of 2,2-dimethyl-7-chloroheptanenitrile (88%) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 3.57 (t, J = 6.6 Hz, 2H), 1.92-1.72 (m, 2H), 1.58-1.44 (m, 6H), 1.36 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6940-78-9, its application will become more common.

Reference:
Article; Liu, Peng; Xu, Xing; Chen, Lili; Ma, Lei; Shen, Xu; Hu, Lihong; Bioorganic and Medicinal Chemistry; vol. 22; 5; (2014); p. 1596 – 1607;,
Chloride – Wikipedia,
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Electric Literature of 18282-59-2, A common heterocyclic compound, 18282-59-2, name is 4-Bromo-1,2-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

Tris [(DIBENZYLIDINEACETONE)] di palladium (0) (5 molpercent ; 23 mg) was added to a mixture of 1- [[4- (3-PIPERIDIN-1-YL-PROPOXY)-PHENYL]-PIPERAZINE (D11)] (150 mg; 0.49 [MMOL),] 3, 4-dichloro bromo benzene (160 mg; 1.2 eq), sodium [TERT-BUTOXIDE] (71 mg; 1.1 eq) and racemic 2,2′- bis (diphenylphosphino)-1, 1′-binaphthyl (7.5 molpercent ; 24 mg) in dry [TOLUENE] [(3ML).] The resulting mixture was heated at reflux under argon for 18 hours. The reaction was allowed to cool to room temperature and diluted with ethyl acetate (10 ml). The resulting solids were removed by filtration and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica eluting with 3percent methanol in [DICHLOROMETHANE] to afford the title compound as a buff solid (45 mg) MS (ES+) [M/E] 448 [M+H] +.

The synthetic route of 18282-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/35556; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 121-27-7, The chemical industry reduces the impact on the environment during synthesis 121-27-7, name is 5-Chloro-2-(4-chlorophenoxy)aniline, I believe this compound will play a more active role in future production and life.

A solution of 8 (2.56 g, 10.1 mmol), ethyl bromoacetate (7.0 mL, 63 mmol), and N,N-diisopropylethylamine (7.0 mL, 41 mmol) was stirred at 140 C for 5 h. The reaction mixture was cooled down, and diluted with EtOAc (100 mL). The organic layer was washed with 10% aqueous citric acid (100 mL * 2), saturated aqueous NaHCO3, and brine, and dried over MgSO4. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The residue oil was purified by silica gel column chromatography (hexane/EtOAc = 95:5 to 80:20) to afford 9 (3.68 g, 85%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): delta (ppm) 1.20 (t, J = 7.2, 6H), 4.10 (s, 4H), 4.11 (q, J = 7.2, 4H), 6.76 (d, J = 8.7, 1H), 6.81-6.87 (m, 4H), 7.24 (d, J = 8.7, 2H). 13C NMR (100 MHz, CDCl3): delta (ppm) 14.15, 54.04, 60.95, 118.72, 119.42, 121.65, 122.31, 127.95, 129.56, 129.94, 142.40, 145.35, 155.99, 170.52. LC-MS (ESI) m/z 426, 428 [M+H]+.

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-Chloro-2-(4-chlorophenoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nakao, Akira; Suzuki, Hiroko; Ueno, Hiroaki; Iwasaki, Hiroshi; Setsuta, Tomofumi; Kashima, Akiko; Sunada, Shinji; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4952 – 4969;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 5013-77-4,Some common heterocyclic compound, 5013-77-4, name is N-Methyl-2,4-dichlorobenzylamine, molecular formula is C8H9Cl2N, 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: 6.11. 4-Chloro-N-(2,4-dichlorobenzyl)pyrimidin-2-amine (13) and 2-chloro-N-(2,4-dichlorobenzyl)pyrimidin-4-amine (14); 2,4-Dichlorobenzylamine (1.0 mL, 7.4 mmol) was added to a stirring solution of 2,4-dichloropyrimidine (1.0 g, 6.7 mmol) and DIPEA (1.8mL, 10.1mmol) in anhydrous DCE (10mL) and the reaction mixture was stirred at 20C under a nitrogen atmosphere for 24h. LCMS showed the presence of a mixture of regioisomers (System A, RT=1.10min, 63% and 1.25min, 27%). The reaction mixture was diluted with water (50mL) and extracted with DCM (3×50mL). The combined organic extracts were washed with brine (50mL), dried using a hydrophobic frit and evaporated under reduced pressure. The residue was purified by column chromatography on a silica column, using a gradient of 0-100% ethyl acetate-cyclohexane over 40 min. The appropriate fractions were combined and evaporated under reduced pressure to afford the two regioisomers as white solids: less-polar isomer 13 (400 mg, 21%) and the more-polar isomer 14 (950 mg, 49%); 6.23 2-Chloro-N-(2,4-dichlorobenzyl)-N-methylpyrimidin-4-amine (24) Prepared from 12 (0.50 g, 3.4 mmol), N-methyl-(2,4-dichlorobenzyl)amine (0.64 g, 3.4 mmol) and DIPEA (1.3 mL, 7.4 mmol) according to the procedure described for the preparation of 14 to give 24 (0.39 g, 38%) as a white solid: 1H NMR delta (400 MHz, CD3OD) 8.04 (br. s, 1H), 7.52 (d, J = 2.0 Hz, 1H), 7.31 (dd, J = 8.0, 2.0 Hz, 1H), 7.12 (d, J = 8.0 Hz, 1H), 6.66 (br. s, 1H), 4.89 (s, 2H) (obscured by HOCD3), 3.13 (br. s, 3H); LCMS (System A, UV, ES) RT = 1.28 min, [M + H]+ = 302, 304, 306, 100% purity.

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

Reference:
Article; Shukla, Lena; Ajram, Laura A.; Begg, Malcolm; Evans, Brian; Graves, Rebecca H.; Hodgson, Simon T.; Lynn, Sean M.; Miah, Afjal H.; Percy, Jonathan M.; Procopiou, Panayiotis A.; Richards, Stephen A.; Slack, Robert J.; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 14 – 25;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 622-86-6, A common heterocyclic compound, 622-86-6, name is (2-Chloroethoxy)benzene, molecular formula is C8H9ClO, 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.

2-Bromophenyl acetic acid (5.0 g, 23.3 mmol,)was suspended in trifluoroacetic anhydride (13.5 mL, 93.5 mmol).Chloroethyoxylbenzene (3.3 mL, 23.3 mmol) was added to the stirred suspensiondropwise. The resulting mixture was allowed to stir overnight at roomtemperature. The reaction was quenched with 40% aqueous sodium hydroxidesolution and then extracted with ethyl acetate (2 x 20 mL). The combined organic layers were dried overanhydrous magnesium sulfate and concentrated on a rotary evaporator. The resulting residue was purified bychromatography on silica gel (ethyl acetate/hexane) to afford 5.98 g (73%) ofthe desired product as a light orange solid. 1H NMR (400 MHz, CDCl3)delta 8.05 (d, J = 8.9 Hz, 2H), 7.60 (d, J = 8.5 Hz, 1H), 7.24 (m, 2H), 7.18 (m,1H), 6.96 (d, J = 9.0 Hz, 2H), 4.40 (s, 2H), 4.37 (t, J = 5.5 Hz, 2H), 3.88 (t,J = 5.7 Hz, 2H); MS (ESI) (m/z) 354.0/356.0 (M+H)+.

The synthetic route of 622-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Childers, Wayne; Fan, Rong; Martinez, Rogelio; Colussi, Dennis J.; Melenski, Edward; Liu, Yuxiao; Gordon, John; Abou-Gharbia, Magid; Jacobson, Marlene A.; Bioorganic and Medicinal Chemistry Letters; vol. 30; 2; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3843-97-8, name is 5-Chloro-2-ethylaniline, belongs to chlorides-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 3843-97-8, Quality Control of 5-Chloro-2-ethylaniline

Step 4: 4-Chloro-1-ethyl-2-iodobenzeneA mixture of 5-chloro-2-ethylaniline (3.35 g, 21.5 mmol), p-toluensulfonic acid (12.29 g, 64.6 mmol) and water (2.15 mL) were ground in a mortar for few minutes, to obtain a homogeneous paste to which solid sodium nitrite (3.71 g, 53.8 mmol) was added and the paste ground for 10 min. Solid potassium iodide (8.94 g, 53.8 mmol) was added and the paste ground for 20 min. The paste was then dissolved in water (50 mL) and treated with sodium sulfite (10% aq. sol.), before being extracted with EtOAc (3 x 100 mL). The combined organic layers were dried over sodium sulfate and the crude was purified by flash chromatography (hexane) to obtain the title compound as a light-yellow oil (4.35 g, 76%).1H NMR (400 MHz, DMSO- /6) delta ppm 1.12 (t, J=7.51 Hz, 3 H), 2.66 (q, J=7.53 Hz, 2 H), 7.29 – 7.35 (m, 1 H), 7.42 (dd, J=8.30, 2.20 Hz, 1 H), 7.87 (d, J=2.20 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-2-ethylaniline, and friends who are interested can also refer to it.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; BRASCA, Maria Gabriella; BANDIERA, Tiziano; BERTRAND, Jay Aaron; GNOCCHI, Paola; MIRIZZI, Danilo; NESI, Marcella; PANZERI, Achille; WO2012/143248; (2012); A1;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, belongs to chlorides-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 13918-92-8, Recommanded Product: 2,4-Difluorobenzene-1-sulfonyl chloride

c) lambda/-[5-bromo-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide; To a cooled (0 0C) solution of 5-bromo-2-(methyloxy)-3-pyridinamine (20.3 g, 100 mmol) in pyridine (200 mL) was added slowly 2,4-difluorobenzenesulfonyl chloride (21.3 g, 100 mmol) over 15 min (reaction became heterogeneous). The ice bath was removed and the reaction was stirred at ambient temperature for 16 h, at which time the reaction was diluted with water (500 mL) and the solids filtered off and washed with copious amounts of water. The precipitate was dried in a vacuum oven at 50 0C to give N-[5-bromo-2-(methyloxy)-3-pyridinyl]-2,4- difluorobenzenesulfonamide (12 g, 31.6 mmol, 31.7 % yield) MS(ES)+ m/e 379.0, 380.9 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Difluorobenzene-1-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/55418; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

96558-78-0, name is 3-Bromo-5-chlorophenylamine, belongs to chlorides-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: C6H5BrClN

To a solution of compound 1 (50 g, 242.2 mmol, 1 eq ) in 1 L of toluene and 100 mL of H2O was added potassium cyclopropyl(trifluoro)boranuide (39.4 g, 266.4 mmol, 1.1 eq), t- BuOK (81.5 g, 726.5 mmol, 3 eq) and Pd(dppf)Cl2.CH2Cl2 (19.8 g, 24.2 mmol, 0.1 eq) and purged with N2 for 3 times. The mixture was stirred at 90C for 16 hours. Then it was filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography (S1O2, eluting with a gradient of petroleum ether:ethyl acetate =1:0 to 3:1) to get 37.5 g of compound 2 (223.7 mmol, 92.4% yield) as a yellow oil.

The synthetic route of 96558-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; VACCA, Joseph, P.; WAGER, Travis, T.; (383 pag.)WO2020/117877; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 64628-73-5, name is 3-Chloro-4-(trifluoromethoxy)aniline, belongs to chlorides-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 64628-73-5, Product Details of 64628-73-5

H. Synthesis of (6S)-6-({6-[3-chloro-4-(trifluoromethoxy)phenyl]-3-pyridinyl}methoxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (28) by the method of Scheme 4 An ice-cold mixture of 98% H2SO4 (0.75 mL) and water (2.25 mL) was added to 3-chloro-4-(trifluoromethoxy)aniline (53) (1.00 g, 4.73 mmol) and the resulting salt was crushed (using a glass rod) and cooled in an ice bath. A solution of NaNO2 (359 mg, 5.20 mmol) in cold water (0.75 mL, then 0.25 mL) was added drop-wise, and the mixture was stirred at 0 C. for 12 min. A solution of urea (42.6 mg, 0.709 mmol) in cold water (0.25 mL) was added, and the mixture was stirred at 0 C. for 3 min. Finally, a solution of KI (1.65 g, 9.94 mmol) in cold water (1.6 mL, then 0.2 mL) was added slowly, and the mixture was stirred at room temperature for 10 min, and then at 52 C. for 2 h. The resulting cooled mixture was diluted with ice-water (45 mL) and extracted with CH2Cl2 (4*50 mL). The extracts were sequentially washed with an aqueous solution of Na2SO3 (30 mL of 0.5%) and then with water (40 mL) and finally concentrated carefully under reduced pressure at 17 C. The resulting oil was chromatographed on silica gel, eluting with pentane, to give 2-chloro-4-iodo-1-(trifluoromethoxy)benzene (54) (1.24 g, 81%) as a colourless oil (a white solid on freezing); 1H NMR (CDCl3) delta 7.82 (d, J=2.1 Hz, 1H), 7.61 (dd, J=8.6, 2.1 Hz, 1H), 7.05 (dq, J=8.6, 2.0 Hz, 1H); HRAPCIMS calcd for C7H3ClF3IO m/z (M+) 323.8834, 321.8864, found 323.8834, 321.8861.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-4-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Global Alliance for TB Drug Development; US2012/28973; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 553-82-2, 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. 553-82-2, name is 2,4-Dichloro-1-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To synthesize compound 96, to 2,4-dichloroanisole (5 mL, 36 mmol) in THF (22 mL) at -78 C. was added 2.5 M nBuLi (17 mL, 43 mmol) keeping the temperature below -65 C. After 30 min, the reaction was poured into frozen (-78 C.) trimethylborate (14 mL, 215 mmol) followed by another portion of trimethylborate (10 mL, 90 mmol) and allowed to warm to room temperature over 16 h. The solid suspension was poured into a 1 N HCl aqueous solution and stirred for 1 h. The suspension was filtered to give 3.6 g (46%) of a white solid contaminated most likely with B(OH)4. A second batch of crystals formed which were collected as an off-white solid that was compound 96 (5.8 g, 74%). 1H NMR DMSO-d6: delta 8.53 (s, 2H), 7.29 (d, J=8.8 Hz, 1H), 7.06 (d, J=8.8 Hz, 1H), 3.83 (s, 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, 2,4-Dichloro-1-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TargeGen, Inc.; US2005/245524; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics