Category: chlorides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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 1871-57-4, Quality Control of 3-Chloro-2-chloromethyl-1-propene

General procedure: To a cooled solution (5 C) of the corresponding 4,6-O-(R)-benzylidene-d-hexopyranoside derivative (obtained using the procedure describe by our group2c) (35.4 mmol) in dry THF (70 mL) were added, successively, freshly powdered potassium hydroxide (7.0 g, 125 mmol), 18-crown-6 (0.38 g, 1.4 mmol), and 3-chloro-2-chloromethylpropene (4.1 mL, 35.4 mmol). The reaction mixture was stirred at this temperature for 3 h, and left at room temperature until all the starting material had been consumed, as monitored by TLC (5-7 days, approximately), then diluted with dichloromethane (60 mL) and washed successively with water and aqueous saturated solution of sodium bicarbonate, dried (MgSO4), filtered, and the filtrate was evaporated to dryness.

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, 3-Chloro-2-chloromethyl-1-propene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Vega-Perez, Jose M.; Vega-Holm, Margarita; Perinan, Ignacio; Palo-Nieto, Carlos; Iglesias-Guerra, Fernando; Tetrahedron; vol. 67; 2; (2011); p. 364 – 372;,
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These common heterocyclic compound, 344-19-4, name is 2,6-Dichloro-4-fluoroaniline, 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. Formula: C6H4Cl2FN

Preparation 10 2,6 Dichloro-4-fluoro-phenylhydrazine hydrochlorideTo a 0 0C solution of 2,6 Dichloro-4-fluorophenylamine (3.0 g, 16.6 mmol) in 12 M HCl (30 mL) and TFA (20 mL) is added slowly and dropwise NaNO2 (20 mmol, 1.37 mL) in water (6 mL). The reaction is stirred at 0 0C for 1 h. A solution of SnCl2 (5.74 g, 25.6 mmol) in 12 M HCl (16 mL) is added over 15 minutes. The ice bath is removed and the reaction is stirred for 18 h. The reaction is filtered and the solid is washed with isopropyl alcohol. The solid is dried to yield the title compound (3.0 g, 96 %). LC-ES/MS m/e 194.0 (M+ 1)

The synthetic route of 2,6-Dichloro-4-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/140183; (2007); A1;,
Chloride – Wikipedia,
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Reference of 13526-66-4, These common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, 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.

Preparation of trans-4-(3-bromoimidazo[1,2-b]pyridazin-6-ylamino)cyclohexanol To 6-chloro-3-bromoimidazo[1,2-b]pyridazine (1.00 g, 4.30 mmol, 1.0 equiv) and p-TSA (818 mg, 4.30 mmol, 1.0 equiv) in DMSO (7.00 mL) was added trans-4-aminocyclohexanol (1.49 g, 12.9 mmol, 3.0 equiv). The mixture was heated at 100 C. for 24 h. Purification by column chromatography using 5% methanol in dichloromethane elution gave 1.1 g of the yellow solid, 83%.

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Califia Bio, Inc.; GOODFELLOW, VAL S.; NGUYEN, THONG X.; RAVULA, SATHEESH B.; GELBARD, HARRIS A.; US2014/256733; (2014); A1;,
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Electric Literature of 57310-39-1,Some common heterocyclic compound, 57310-39-1, name is 3-Bromo-4-chlorotoluene, molecular formula is C7H6BrCl, 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 7: 4-(2′-Chloro-5′-methyl-biphenyl-4-ylmethyl)-2-phenyl-morpholine; 109mg of 4-(4-Bromo-benzyl)-2-phenyl-morpholine was combined with 102mg of bis(pinacolato)diboron, 97mg of potassium acetate, l lmg tetrakis(triphenylphosphine)palladium(0), and 1.9mL DMF. The mixture was heated in a microwave reactor at 12O0C for 7 minutes and cooled. 0.8mL of 2M aqueous sodium bicarbonate was added along with lOlmg of 3-Bromo-4-chlorotoluene in 0.15mL DMF. The mixture was heated in the microwave reactor for an additional 5 minutes at 120C. The reaction was cooled and filtered through Celite, washing with methylene chloride. The eluant was concentrated and purified by flash chromatography twice using an ethyl acetate/hexanes gradient to afford 3.5mg of product. ES MS (+) m/z 378

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-chlorotoluene, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2007/70760; (2007); A2;,
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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. 5013-77-4, name is N-Methyl-2,4-dichlorobenzylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of N-Methyl-2,4-dichlorobenzylamine

General procedure: To a stirring solution of carboxylic acid (10 mmol, 1.0equiv) in dry DMF (10 mL) in a two-neck flask under argon atmosphere at -10 oC, HOBt (hydrate form, 1.76 g, 13 mmol,1.3 equiv) was added followed by the addition of DIPEA (2.26 mL, 13 mmol, 1.3 equiv) and EDCI (2.02 g, 13 mmol, 1.3equiv). The reaction mixture was stirred at -10 oC for 30 min before an appropriate amine (10 mmol, 1.0 equiv) was addedand allowed to warm to room temperature. After 16 h, the reaction mixture was treated with 10% citric acid solution (25mL) and extracted with DCM. The organic phase was washed with saturated NaHCO3 solution (2 ×), followed with waterand brine, dried over anhydrous Na2SO4, filtered, and evaporated in vacuo to remove solvents. The crude product waspurified by silica gel flash chromatography (EtOAc-Heptane).

The synthetic route of 5013-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mai, Anh Hung; Pawar, Sonalika; De Borggraeve, Wim M.; Tetrahedron Letters; vol. 55; 33; (2014); p. 4664 – 4666;,
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These common heterocyclic compound, 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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. Safety of 5-Chloro-1H-benzo[d][1,2,3]triazole

General procedure: in EtOAc/MeOH (4:1) mixture solvent (2 mL), benzotriazoles 1 (0.3 mmol), sodium sulfinates 2 (0.54 mmol), NaBr (0.36 mmol) and mCPBA (0.39 mmol) were added successively. The suspension mixture was vigorously stirred at room temperature for 4 h. Upon completion, the reaction was quenched by addition of sat. aq. Na2S2O3 (2 mL), basified with sat. aq. Na2CO3(8 mL) and H2O (5 mL). The mixture was extracted with CH2Cl2 (3×5 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified by TLC technique (3:1 (v/v) petroleum ether/ethyl acetate) to furnish sulfonylbenzotriazoles 3.

The synthetic route of 5-Chloro-1H-benzo[d][1,2,3]triazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Sixue; Zhang, Yikun; Yan, Jie; Synthetic Communications; vol. 46; 17; (2016); p. 1432 – 1437;,
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Synthetic Route of 2613-30-1, The chemical industry reduces the impact on the environment during synthesis 2613-30-1, name is 4-Chloro-2,5-difluoroaniline, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 1H-pyrrolo[3,2-H]quinoline-3-sulfonyl chloride (140 mg, 0.52 mmol) in pyridine (1.5 mL) was added 4-chloro-2,5-difluoroaniline (90 mg, 0.55 mmol). The reaction mixture was stirred at room temperature for 4h and then evaporated to dryness. The residue was triturated in a mixture of water/acetonitrile (8/2) and sonicated. The solid suspension was filtered, rinsed with water, dried under vacuum at 35C, to afford 105 mgof N-(4-chloro-2,5-difluorophenyl)-1 H-pyrrolo[3,2-h]quinoline-3-sulfonamide 1-118, as a beige solid.Yield: 50%.Basic LCMS Method 1 (ES): 394 (M+H), 99 % purity.1H NMR (400 MHz, DMSO-d6) 6 13.26 (s, 1H), 10.51 (s, 1H), 8.93 (dd, J = 4.4, 1.6 Hz,1 H), 8.46 (dd, J = 8.3, 1.6 Hz, 1 H), 8.04 – 7.65 (m, 3H), 7.59 (m, 1 H), 7.51 (dd, J = 9.8,6.8 Hz, 1H), 7.40 (dd, J = 10.4, 7.0 Hz, 1H).

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-Chloro-2,5-difluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); A1;,
Chloride – Wikipedia,
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Electric Literature of 50638-47-6, 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. 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a magnetically stirring solution of 4-bromo-2-chloroanisole (0.50 g, 2.61 mmol) and 1- CYCLOPENTYL-2-PROPEN-1-OL (1.5 eq, 0.49 g, 3.88 mmol) in anhydrous N-methylpyrrolidinone (3.0 mL), under argon at room temperature, was added sodium bicarbonate (1.2 eq, 0.26 g, 3.10 mmol) followed by DICHLOROBIS (TRIPHENYLPHOSPHINE) PALLADIUM (II) (0.02 eq, 36.7 mg, 0.05 MMOL). The resulting mixture was heated to 140 C in an oil bath and maintained for 4 hours. The resulting dark reaction mixture was cooled to room temperature and poured into water (50 mL) and extracted with EtOAc (2 X 25 mL). The organics were washed with water (50 mL) and brine (50 mL) then dried over NA2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (1% through 10% EtOAc in Hexanes) to yield the intermediate ketone as a slightly yellow oil (0.49 g, 79%).

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-chloro-1-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2004/74270; (2004); A2;,
Chloride – Wikipedia,
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Application of 1996-29-8,Some common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-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.

Under a nitrogen atmosphere, 104.7 g of 2-fluoro-4-chlorobromobenzene, 400 ml of THF and 67.3 g of potassium t-butoxide were added to a 1 L three-necked flask.After cooling to -60 C, 300 mL of n-butyl lithium solution (2 mol / L) was added dropwise, and the addition was completed -50 to -60 CAfter heat preservation for 1 h, the temperature was raised to -30 C, and then 172.6 g of tributyl borate was added dropwise.After the completion of the dropwise addition, the temperature was naturally raised to room temperature for 2 hours.The reaction solution is acidified with hydrochloric acid, extracted with petroleum ether, and washed with water.Concentrated to a white solid a-1, 75.1 g, Y = 86.1%,LC = 98.15%. 2) Synthesis of a-2: under nitrogen protection,Add a-1 41.9g to a 250ml three-necked bottle.4-bromo resorcinol37.8g, potassium carbonate 27.6g,TBAB 2.0g, Pd(0) 0.5g, ethanol 100mL, water 50mL,After stirring at reflux for 3 h, the reaction solution was acidified with dilute hydrochloric acid.Extracted with ethyl acetate and concentrated.Recrystallization from 2 times ethanol gave a white solid a-2.38.5 g, Y = 80.7%, GC = 98.78%. 3) Synthesis of a-3: under nitrogen protection,Add a-223.9g to a 100ml three-necked bottle.DMF 70mL, 60% sodium hydride 8.0g,Reflow reaction for 0.5 h,The reaction solution was poured into ice water, neutralized with dilute hydrochloric acid, and extracted with ethyl acetate, and evaporated to give a yellow solid a-3, 20.9 g,GC=98.61% 4) Synthesis of a-4: A-320.9 g was sequentially added to a 100 ml three-necked flask.60 mL of dichloromethane,21.7 g of trimethylchlorosilane, reacted at room temperature for 0.5 h, concentrated,A yellow solid a-4, 27.8 g, Y = 100%, GC = 98.65%. 5) Synthesis of a-5: under nitrogen protection,Add a-423.3g to a 250 mL three-necked flask.THF 100ml, potassium t-butoxide 10.8g, after cooling to -50 C,60 mL of n-butyllithium solution (2 mol/L) was added dropwise.After the addition is completed, the temperature is kept at -50 to -40 C for 1 h.After heating to -30 C, 27.6 g of tributyl borate was added dropwise.After the completion of the dropwise addition, the temperature was naturally raised to room temperature for 2 hours. The reaction mixture was acidified with hydrochloric acid, extracted with EtOAc EtOAc.Y = 74.2%, LC = 98.66%. 6) Synthesis of a-6: Under nitrogen protection, 4-bromo resorcinol 9.5 g, a-5 17.8 g, potassium carbonate 13.8 g, TBAB 1.0 g were sequentially added to a 100 ml three-necked flask.Pd(0)0.2g, ethanol 50mL, water 20mL, reflux and stirring for 5h,The reaction solution was acidified with dilute hydrochloric acid, extracted with toluene, and concentrated.Recrystallization from 2 times ethanol gave a pale yellow solid a-6.13.1 g, Y = 71.9%, GC = 99.18%. 7) Synthesis of a-7: A-6 10.9 g was added to a 100 ml three-necked bottle in turn.50mL of dichloromethane, 9.4g of tetrabutylammonium fluoride,The reaction was refluxed for 1 h, washed with water and concentrated to give a pale yellow solid a-7.8.1 g, Y = 92.0%, LC = 98.76%. 8) Synthesis of a: under nitrogen protection,Add a-75.8g to a 100ml three-necked bottle.50 mL of dichloromethane and 9.1 g of triethylamine.The polymerization inhibitor is 0.01 g of hydroquinone, and a mixed solution of 7.5 g of methacryloyl chloride and 15 mL of dichloromethane is added dropwise in an ice water bath, and the mixture is naturally added to room temperature and stirred for 0.5 h after the dropwise addition.The reaction solution is acidified with dilute hydrochloric acid, washed with water and concentrated.Recrystallization from 1x ethanol and 2 times n-heptane mixed solvent,Purified by silica gel column to obtain product a, 5.2g, Y=52.5%,LC = 99.90%.

The synthetic route of 1996-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xi’an Ruili Electronic Materials Co., Ltd.; Li Chao; Zhao Wen; Zhang Yanli; Jin Linuo; (35 pag.)CN109503534; (2019); 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. 1205-71-6, name is 4-Chloro-N-phenylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H10ClN

In a 250ml round bottom flask,10-bromobenzo [b] naphtho [2,1-d] furan (12 mmol), copper iodide (15 mmol), potassium tert-butoxide (65 mmol),1,2-diaminocyclohexane (12 mmol)And (4-chloro-phenyl) -phenylamine (12 mmol) were added to dry 1,4-dioxane (100 ml) and refluxed for 48 hours under N2 atmosphere. The obtained intermediate was cooled to room temperature, and added Water was then filtered through a pad of diatomaceous earth while being extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate. After filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain the intermediate HT002-1.

The synthetic route of 1205-71-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Tianma Organic Shine Display Co., Ltd.; Zhang Lei; Gao Wei; Niu Jinghua; Dai Wenpeng; Xiao Wenjing; Lu Yan; Zhu Hongyan; (28 pag.)CN110746391; (2020); A;,
Chloride – Wikipedia,
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