Category: chlorides-buliding-blocks

Synthetic Route of 461432-23-5,Some common heterocyclic compound, 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, molecular formula is C15H14BrClO, 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.

Under nitrogen protection, in a 250 ml three-necked flask (numbered bottle A) was added 5-bromo-2-chloro-4′-ethoxydiphenylmethane (III-1) (12.5, 0.038 mol), 40 ml of dry tetrahydrofuran. And 80 ml of toluene (dried by chlorination of hydrazine), and the dried ice acetone was cooled to -72 C with stirring, and a 2.5 Mu n-BuLi n-hexane solution (18.4 ml, 0.046 mol) was added dropwise to ensure that the temperature was not higher than -60 C, stir for 30 min. Prepare a 500ml three-neck bottle (No. B), nitrogen protection, add 2,3,4,6-tetra-O-trimethylsilyl-FD-gluconolactone (19.7g, 0.042mol) and 110ml toluene (dried by chlorination of hydrazine), dry ice acetone was cooled to -72V. After the reaction time in the bottle A was reached, the solution in the bottle A was introduced into the bottle B, the reaction was continued for 2 hours at a low temperature, methanesulfonic acid (14.8 g, 0.154 mol) and 110 ml of methanol were added, and the dry ice bath was removed, and the temperature was naturally raised to room temperature. The reaction was overnight. After completion of the reaction, a saturated sodium hydrogencarbonate solution was added to adjust the pH to neutrality. After separation, the aqueous phase was extracted with ethyl acetate. The organic phase was washed once with saturated sodium chloride and dried over anhydrous sodium sulfate. After suction filtration, the solvent was evaporated, and after chromatography, 10.8 g (64.3%) of white foam solids were obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, its application will become more common.

Reference:
Patent; Huarun Shuang He Pharmaceutical Co., Ltd.; Zhai Jianguo; He Yang; Zhu Yingjie; Zhou Yisui; Ma Hongmin; Song Meng; (46 pag.)CN108218928; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 39989-43-0, name is 3,5-Dichlorobenzylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 3,5-Dichlorobenzylamine

Example 28 – Synthesis of Compound 24 (S)-9-fluorenylmethyl 10-(3,5-dichlorobenzyl)- 2,2-dimethyl-4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaiscos-19-en-8-ylcarbamate24(lSr)-9-fluorenylmethyl 10-(3,5-dichlorobenzyl)-2,2-dimethyl- 4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaiscos-19-en-8- ylcarbamateTo 3,5-dichlorobenzylamine (0.49 g, 2.8 mmol) in DCM (5 ml_) was added the alpha,beta- unsaturated ketone 23 (2.12 mmol) in DCM (10 ml_). After stirring at room temperature for 15 mins, Fmoc-diaminobutyric acid(Boc)-OH (1.35 g, 3.1 mmol) and DIC (0.5 ml_, 3.2 mmol) was added. The reaction was stirred at room temperature overnight. The DCM was removed by rotary evaporation and the residue was subjected to column chromatography on silica gel using petroleum spirit:EtOAc (1 :1 to 0:1 ), providing compound 24 (0.48 g, 22%).

The synthetic route of 39989-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MIMETICA PTY LTD; BLASKOVICH, Mark, Arnold, Thomas; CASSIDY, Peter, Joseph; WO2010/96853; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 10061-02-6, 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 10061-02-6 as follows.

A reactor was charged with 1.0 kg (9.0 mol) of trans-1, 3-dicloropropene, 3 L of acetonitrile and 1.02 kg (10 mol) of sodium bromide. The suspension was heated to reflux for at least 24 hours, then cooled to 20/250C at the end of the reaction; the salts were filtered and washed with 2 x 500 mL of acetonitrile. The filtrate was distilled through a Vigreux column at atmospheric pressure and internal temperature of 80/l00C to remove the acetonitrile, getting 1.096 kg of a dark orange oil. Weight composition by 1H-NMR: 89% of trans-3-bromo-l- chloropropene, 8% of trans-1, 3 -dicloropropene and 3% of solvent. 1H NMR (CDC13) delta: 3.93 (m, 2H, CH2), 6.14 (m, IH, CH), 6.33 (dt, IH, CHCl). MS (EI) m/z: 156 (M+), 77.

According to the analysis of related databases, 10061-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F.I.S. FABBRICA ITALIANA SINTETICI S.p.A; WO2008/6394; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 501-29-1, 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 501-29-1 as follows.

A mixture of 4-chloro-3-fluoroanisole (2.52 g, 15.7 mmol, 1.0 eq.), silver trifluoroacetate (8.57 g, 38.8 mmol, 2.5 eq.), iodine (7.95 g, 31.3 mmol, 2.0 eq.) and chloroform (100 mL) is stirred at r.t. for 16h. The reaction mixture is filtered through a silica plug on a fritted funnel and rinsed with chloroform. The filtrate is washed successively with an aqueous solution of Na2S2O3, water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel to afford the expected product

According to the analysis of related databases, 501-29-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALAPAGOS NV; LES LABORATOIRES SERVIER; LABEGUERE, Frederic, Gilbert; HENG, Rama; DE CEUNINCK, Frederic, Andre; ALVEY, Luke, Jonathan; AMANTINI, David; BREBION, Franck, Laurent; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene; PEIXOTO, Christophe; POP-BOTEZ, Iuliana, Ecaterina; VARIN, Marie, Laurence, Claire; (180 pag.)WO2017/211666; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 4584-46-7, 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. 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2-(2,4-dimethoxy-benzyl)-4-hydroxy-isoindole-1,3-dione (317 mg, 1.01 mmol), 2-dimethylaminoethyl chloride hydrochloride (160 mg, 1.11 mmol) and potassium carbonate (350 mg, 2.5 mmol) in DMF (4 mL) was heated at 60 C. for 18 hours. The mixture was concentrated in vacuo, taken up in ethyl acetate and extracted twice with 1N hydrochloric acid. The aqueous extracts were made basic with solid potassium carbonate and extracted with ethyl acetate (×2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to give the title compound (236 mg, 61%) as an off-white solid. 1H NMR (methanol-d4) 7.73 (1H, t), 7.44-7.40 (2H, m), 7.02 (1H, d), 6.51 (1H, d), 6.42 (1H, dd), 4.72 (2H, s), 4.33 (2H, t), 3.80 (3H, s), 3.76 (3H, s), 2.87 (2H, t), 2.40 (6H, s). MS: [M+H]+ 385.

The synthetic route of 2-Chloro-N,N-dimethylethanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H3BrClF

(2) The corresponding arylmagnesium bromide was prepared from 406 g (1.94 mol) of 4-bromo-2-chlorofluorobenzene and 48.6 g (2.00 mol) of magnesium turnings in 1,300 ml of anhydrous tetrahydrofuran by the customary process. The solution thus obtained was added dropwise to a solution of 278.3 g (2.3 mol) of allyl bromide in 200 ml of anhydrous tetrahydrofuran at 30-45 C. The mixture was then heated under reflux for 0.5 h, allowed to stand at room temperature for 16 h and poured onto 1.5 liters of ice-water. After acidification using a little 2N hydrochloric acid, the mixture was extracted twice using 1 liter of hexane each time. The extracts were washed three times with water, dried over Na2 SO4 and evaporated. The residue yielded 235 g (71%) of 3-(3-chloro-4-fluorophenyl)propene of b.p.10 =72 C. with a purity of 98.7% (determined by gas chromatography) on subsequent distillation.

The synthetic route of 60811-21-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US4920212; (1990); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 883499-24-9, 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. 883499-24-9, name is 1-Bromo-2-chloro-3-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mechanical-stirred solution of diisopropylamine (5.02 g, 7.08 ml, 49.7 mmol, Eq:1.04) in THF (35 ml) was added dropwise (5 mm) at -20C n-butyllithium, 1.6 M in hexane (31ml, 49.7 mmol, Eq: 1.04) and stirred at 0 C for 20 minutes. The mixture was cooled to -78 Cfollowed by dropwise addition (20 minutes) of a solution of 1-bromo-2-chloro-3-fluorobenzene(10 g, 47.7 mmol, Eq: 1) in THF (10 ml) and the thick yellow suspension was stirred at -78 Cfor 60 mm. Then was added dropwise (5 minutes – exotherm) N,N-dimethylformamide (5.23 g,5.55 ml, 71.6 mmol, Eq: 1.5), the cooling bath was removed and the mixture was allowed to warm to -20 C to give complete conversion. At -20 C the clear yellow solution was quenched with sat NH4C1 (100 ml) and extracted with TBME (100 ml). The aqueous layer was extracted again with TBME (50 ml). The organic layers were dried and evaporated at only 50 mbar forshort time. The yellow residue was dissolved in heptane/ethyl acetate 10:1 (ca. 30 ml) at 55 C,concentrated to 1/3 and stirred to 22 C while crystallisation started. After 30 minutes thesuspension was cooled to 0 C for 30 minutes, the solid was filtered off, washed with heptane (2x 15 ml) and dried (only short time) to give 4-bromo-3-chloro-2-fluorobenzaldehyde (5.27 g,47%) as light yellow solid. The filtrate was evaporated and purified by flash chromatography (silica gel, 70 g, adsorbed on isolute sorbent HM-N, EtOAc in heptane, 0% to 5% ) to give additional compound (4.073 g, 36%) as off-white solid.GC-MS: mlz = 235.9 M.+ (monoisotopic mass 235.90)

The synthetic route of 1-Bromo-2-chloro-3-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; ALANINE, Alexander; BEIGNET, Julien; BLEICHER, Konrad; FASCHING, Bernhard; HILPERT, Hans; HU, Taishan; MACDONALD, Dwight; JACKSON, Stephen; KOLCZEWSKI, Sabine; KROLL, Carsten; SCHAEUBLIN, Adrian; SHEN, Hong; STOLL, Theodor; THOMAS, Helmut; WAHHAB, Amal; ZAMPALONI, Claudia; (623 pag.)WO2017/72062; (2017); A1;,
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Chlorides – an overview | ScienceDirect Topics

Related Products of 39226-96-5, A common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, molecular formula is C8H7ClF3N, 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.

Example 100 N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,2-dimethylpropyl)-5-oxoprolinamide (E100) 1-(2,2-dimethylpropyl)-5-oxoproline (0.100 g, 0.5 mmol, prepared as described below) was dissolved in dichloromethane (5 ml) and to this was added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.191 g, 1 mmol), and 1-hydroxybenzotriazole (0.135 g, 1 mmol). The mixture was stirred for 30 minutes at room temperature and then {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (0.209 g, 1 mmol) was added and the mixture was stirred overnight at room temperature. The mixture was then washed sequentially with water, 3N aqueous citric acid, and three more times with water then dried by filtering through a hydromatrix cartridge (Varian 5 g). The solvent was then evaporated and the residue was purified by mass-directed automated HPLC to give pure N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,2-dimethylpropyl)-5-oxoprolinamide. LC/MS [M+H]+=391/393, retention time=2.78 minutes. N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,2-dimethylpropyl)-5-oxoprolinamide was prepared in an analogous manner to that described for example 100 but using 1-(2,2-dimethylpropyl)-5-oxoproline prepared as described below. LC/MS [M+H]+=391/393, retention time=2.76 minutes.

The synthetic route of 39226-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; US2008/9541; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, 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. Recommanded Product: 39226-96-5

Example 51 N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-methyl-5-oxoprolinamide 1-methyl-5-oxoproline (2.27 g, 15.88 mmol, prepared as described below) was dissolved in dichloromethane (150 ml) and to this was added N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (3.35 g, 17.47 mmol), and 1-hydroxybenzotriazole (2.36 g, 17.47 mmol). The mixture was stirred for ~10 minutes and then triethylamine (2.21 ml, 15.88 mmol) and {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (3.66 ml, 17.47 mmol) were added and the mixture was left stirring at room temperature overnight (~17 hrs). A white precipitate formed during this time. The mixture was then treated with saturated aqueous sodium hydrogen carbonate (~100 ml) and stirred for 10 minutes. The organic layer was separated using a hydrophobic frit and then 2N aqueous hydrogen chloride was added and mixed and separated again. The organic layer was concentrated to give white solids (~2.5 g). The solid was dissolved in ethyl acetate (~200 ml) and washed with water (4*50 ml) followed by brine (50 ml). The organic layer was then dried by passing through a phase separator and concentrated to give pure N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-methyl-5-oxo-L-prolinamide as a fine white solid (2.48 g). LC/MS [M+H]+=335, retention time=2.24 minutes. 1H NMR (CDCl3, 500 MHz) delta 2.02 (m, 1H), 2.35 (m, 1H), 2.39 (m, 1H), 2.47 (m, 1H), 2.81 (s, 3H), 4.00 (dd, 1H, J=8.9, 4.2 Hz), 4.60 (dd, 1H, J=15.1, 6.2 Hz), 4.65 (dd, 1H, J=15.1, 6.2 Hz), 6.56 (broad t, 1H, J=5.8 Hz), 7.38 (t, 1H, J=7.7 Hz), 7.60 (dd, 1H, J=7.6, 1.0 Hz), 7.68 (dd, 1H, J=7.9, 1.2 Hz); 13C NMR delta 176.0, 171.5, 137.5, 133.9, 131.7, 129.3, 127.4, 127.0, 122.8, 63.8, 41.8, 29.4, 29.2, 23.4.

The synthetic route of 39226-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; US2008/9541; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33863-76-2,Some common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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.

steps 1 and 2-A solution of 1-bromo-3-chloro-5-fluoro-benzene (42a, 55 g, 263 mmol) was cooled to 0 C. and treated with a 25% methanolic sodium methoxide solution (68 mL, 315 mmol) and heated to 40 C. for 3 h. The solution was cooled and partitioned between water (1 L) and a 1:1 mixture of hexane/diethyl ether (3×200 mL). The combined extracts were washed with brine (60 mL), dried (Na2SO4), filtered and the solvents evaporated in vacuo to afford 42b as an oil (57.3 g, 92% pure, 238 mmol). The ether 42b (43 g, 173 mmol) was treated with glacial HOAc (150 mL) and 48% aqueous HBr (100 mL) and heated to 120 C. After 40 h, the volatiles were removed while heated to 80 C. and then cooled to RT. The residue was partitioned between water (100 mL) and DCM (3×250 mL). The combined extracts were washed with H2O (50 mL), aqueous NaHCO3 solution (2×50 mL), brine (50 mL), and (MgSO4). The solvents were removed to afford 23.3 g of 42c as a grey solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-chloro-5-fluorobenzene, its application will become more common.

Reference:
Patent; Roche Palo Alto LLC; US2006/25462; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics