Category: 496-16-2

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.496-16-2,2,3-Dihydrobenzo[b]furan,as a common compound, the synthetic route is as follows.

Solid AlCl3 (5.55 g, 0.042 M) was added portionwise to a cold (00C) solution of dihydrobenzofuran (5.0 g, 0.042 M) arid ethyl oxalyl chloride (4.5 mL, 0.042 M) in dry dichloromethane (80 mL). After complete addition the dark solution was warmed up to RT and stirred for 2 hr. The resulting reaction mixture was slowly poured into a concentrated HCl/ice water solution (5 mL/200 mL). The aqueous mixture was stirred for 20 minutes and dichloromethane (1,50 mL) was added. Layers were separated. The aqueous layer was extracted with dichloromethane (1 x). The combined CH2CI2 extracts were dried over MgSO4, filtered, evaporated in vacuo and the crude oil purified by chromatography (Hexane/EtOAc) to provide the desired product as an oil (4.8 g) 54percent. 1H NMR (400 MHz, CDCl3) 87.88 (s, IH), 7.86 (d, J = 8.3 Hz, IH), 6.85 (d, J = 8.8 Hz, IH), 4.72 (t, J = 9 Hz, 2H), 4.45 (q, J = 7.2 Hz, 2H), 3.28 (t, J = 9.2 Hz, 2H), 1.42 (t, J = 7.2 Hz, 3H). MS (m/z): 221 (MH+).

496-16-2, 496-16-2 2,3-Dihydrobenzo[b]furan 10329, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2007/75567; (2007); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

496-16-2, 2,3-Dihydrobenzo[b]furan is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 25.5 g (0.212 mol) of 2, 3-dihydrobenzofuran in 175 mL of acetic acid was added about one quarter of 4.5 mL (0.227 mol) of 70% aqueous nitric acid dropwise. The reaction was monitored by TLC (EtOAc-hexanes (15: 85) ). The mixture was warmed to 70C where the reaction began. The remainder of the nitric acid was then added while maintaining the reaction at 70C. After 30 minutes, the reaction was cooled and poured into 1.5 L of ice water. The black solid was collected by filtration washing with water. The solid was partitioned between 500 mL of saturated aqueous sodium bicarbonate and 150 mL of EtOAc. The aqueous layer was separated and extracted with three 150 mL portions of EtOAc. The combined organic layers were washed with three 100 mL portions of saturated aqueous sodium bicarbonate, 100 mL of saturated aqueous ammonium chloride, 100 mL of brine, dried over magnesium sulfate, filtered, and concentrated to afford a red oil/solid. The mixture was dissolved in dichloromethane and passed through a pad of silica gel eluting with dichloromethane and concentrated. The resulting red mixture was triturated with ether-hexanes (1: 1) and filtered to afford 10.5 g (29%) of 5-nitro-2, 3-dihydrobenzofuran as a tan solid., 496-16-2

The synthetic route of 496-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2003/82787; (2003); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.496-16-2,2,3-Dihydrobenzo[b]furan,as a common compound, the synthetic route is as follows.

Dissolve 2,3-dihydrobenzofuran (1,5 g, 41.6 mmol) in dichloromethane (35 mL),Br2 (6.65 g, 41.6 mmol) was weighed and dissolved in dichloromethane (15 mL). The mixture was added dropwise to the above mixture within 45 minutes at room temperature, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, a saturated NaHSO3 solution (25 mL) was added to quench, and extracted with dichloromethane (15 mL ¡Á 3). The separated organic layer was washed with water, dried over anhydrous Na2SO4, and concentrated under reduced pressure to obtain the target compound as a white solid 7.5 g, yield: 91%. This white solid was 5-bromo-2,3-dihydrobenzofuran (the compound 2)., 496-16-2

The synthetic route of 496-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Taizhou Polytechnic College; Zhang Maofeng; Zhang Yanmei; Wang Lizhong; Wu Xishan; (7 pag.)CN110452201; (2019); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

496-16-2, 2,3-Dihydrobenzo[b]furan is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(1) 4-(2,3-dihydro-1-benzofuran-5-yl)-4-oxobutanoic acid To a suspension of 2,3-dihydro-1-benzofuran (5.2 g) and succinic anhydride (5.2 g) in dichloromethane (30 mL) was gradually added aluminum chloride (14.4 g) under ice-cooling, and the mixture was heated with stirring at 50¡ãC for 0.5 hr. The reaction mixture was cooled, and poured into concentrated hydrochloric acid (100 mL)-ice. The mixture was stirred for 1 hr, and extracted with ethyl acetate. The obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure, and the obtained residue was recrystallized from ethyl acetate to give 4-(2,3-dihydro-1-benzofuran-5-yl)-4-oxobutanoic acid as crystals (3.8 g). 1H-NMR (CDCl3) delta: 2.80 (2H, t, J=6.0 Hz), 3.26(4H, m), 4.67(2H, t, J=9.0 Hz), 6. 82 (1H, d, J=8.4 Hz), 7.85(2H, m)

496-16-2, 496-16-2 2,3-Dihydrobenzo[b]furan 10329, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; EP1845081; (2007); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

496-16-2, 2,3-Dihydrobenzo[b]furan is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation of 1-(2,3-dihydrobenzofuran-5-yl)ethanone Into a 500 mL 3-necked round-bottom flask, was placed a solution of acetyl chloride (62 g) in dry dichloromethane (400 mL). To this was added aluminum(III) chloride (55.6 g, 1.00 equiv). The mixture was allowed to react, with stirring, for 30 min at -10 C. (solution A). Into another 2000 nm 3-necked round-bottom flask, was placed a solution of 2,3-dihydrobenzofuran (50 g, 0.42 mmol, 1.00 equiv) in dry dichloromethane (500 mL) at -10 C. The solution A was added to the above via a cannula, and was stirred for 30 min at 0 C. The mixture was poured into ice/HCl (5:1 v/v, 1 L). The resulting solution was allowed to react, with stirring, for an additional 2 h while the temperature was maintained at room temperature. The resulting solution was extracted three times with 500 mL of CH2Cl2 and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluding through a column with a 1:100 EtOAc/PE solvent system. This resulted in 67 g (94%) of 1-(2,3-dihydrobenzofuran-5-yl)ethanone as a yellow solid., 496-16-2

The synthetic route of 496-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; US2008/318941; (2008); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

496-16-2, 2,3-Dihydrobenzo[b]furan is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a. Preparation of 2,3-dihydrobenzo[b]furan-7-carboxylic acid (15a) To a solution of n-BuLi (1.7 M, 123 ml, 0.21 mol) in 400 ml of hexane at room temperature was added 24.3 g (0.21 mol) of N,N,N’,N’-tetramethylethylenediamine (TMEDA), followed by a hexane (40 ml) solution of 2,3-dihydrobenzo[b]furan (14) (12.56 g, 0.11 mol). The mixture was stirred under argon at room temperature for 4 hours, and then poured into dry ice (pre-washing with anhydrous ether). After stirring at ambient temperature overnight, the mixture was diluted with water (300 ml), and the layers separated. The aqueous layer was acidified with conc. HCl to pH 1, cooled and the precipitate collected on a filter. This was recrystallized from CH2Cl2 to give 15a (9.43 g, 54.7%) as a white solid, mp 167-169.5C., 496-16-2

As the paragraph descriping shows that 496-16-2 is playing an increasingly important role.

Reference£º
Patent; Erbamont Inc.; EP234872; (1991); B1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

496-16-2, 2,3-Dihydrobenzo[b]furan is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of arene (0.5 mmol), I2O5 (334 mg, 1.0 mmol), and KBr (148 mg, 1.25 mmol) was dissolved in 2mL of H2O. The reaction was complete after stirring for the indicated time at room temperature. The mixture was extracted by ethyl acetate and concentrated under reduced pressure, and the mixture was purified by flash column chromatography (silica gel) to afford the desired product., 496-16-2

The synthetic route of 496-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Hou, Jieping; Li, Zejiang; Jia, Xiao-Dong; Liu, Zhong-Quan; Synthetic Communications; vol. 44; 2; (2014); p. 181 – 187;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

496-16-2, 2,3-Dihydrobenzo[b]furan is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 2,3-dihydrobenzo[b]furan (9.4 mL, 83.4 mmol) in dichloromethane (250 mL) under Ar at -5 C. was added dropwise titanium(IV) chloride (18 mL, 167.0 mmol) over 15 min, maintaining the temperature below 0 C. After addition was complete, the red-brown reaction mixture was allowed to stir for a further 10 min before alpha,alpha-dichloromethyl methyl ether (8.3 mL, 91.6 mmol) was added dropwise [CAUTION-exotherm] maintaining the temperature below 0 C. Upon complete addition, the vivid crimson reaction mixture was allowed to warm to ambient temperature over 2 h, and was then cautiously poured onto a saturated aqueous solution of sodium bicarbonate (700 mL). The mixture was filtered through a pad of Kieselguhr, which was washed through with dichloromethane. The phases were separated and the aqueous phase was extracted with dichloromethane (2¡Á400 mL). The combined organic fractions were washed with brine (300 mL), dried (magnesium sulfate) and concentrated in vacuo to afford a mixture [5-CHO:7-CHO (4:1)] of aldehyde products (11.48 g, 93%) as a green-black liquid which as used without further purification., 496-16-2

The synthetic route of 496-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VERNALIS RESEARCH LIMITED; US2005/187282; (2005); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.496-16-2,2,3-Dihydrobenzo[b]furan,as a common compound, the synthetic route is as follows.

To a solution of 2,3-dihydrobenzofuran (1 g, 8.3mmol) in DCM (10mL) was added acetyl chloride (1.3g, 16.6mmol) and AICI3 (3.3g, 24.6mmol) slowly at -10C. The reaction mixture was stirred at -10C for 3h. The TLC showed the reaction to be complete. The reaction mixture was diluted with 5% aqueous HCI (10ml_) and extracted with DCM (3×1 OmL). The combined organic layers were washed with saturated aqueous bicarbonate solution (100ml_), brine (100ml_), dried (Na2S04), filtered and concentrated under reduced pressure to afford 1-(2,3- dihydrobenzofuran-5-yl)ethan-1-one as a brown liquid. Yield: 1.34g (97%); MS (ESI+) for CHNOS m/z 163.0[M+H]+; 1 H NMR (400 MHz, CDCI3): <5 7.86 (s, 1 H), 7.79 (d, J = 8.4Hz, 1 H), 6.80 (d, J = 8.4 Hz, 1 H), 4.66 (t, J = 8.8 Hz, 2H), 3.25 (t, J = 8.8 Hz, 2H), 2.52 (s, 3H)., 496-16-2

The synthetic route of 496-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DISCUVA LTD.; MEO, Paul; KHAN, Nawaz; CHARRIER, Cedric; (252 pag.)WO2019/86890; (2019); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.496-16-2,2,3-Dihydrobenzo[b]furan,as a common compound, the synthetic route is as follows.

EXAMPLE 4 Preparation of 2,3-dihydrobenzofuran-5-sulfonyl chloride Sulfur trioxide-N,N-dimethylformamide complex (9.2 g, 60 mmoles) and N,N-dimethylformamide (20 ml) were added to a 250 ml, 3-necked flask under nitrogen purge. The solution was stirred at room temperature and 2,3-dihydrobenzofuran (6.0 g, 50 mmoles) was added dropwise. The solution was slowly heated to 85¡ã-90¡ã C. over the course of one hour. The light brown solution was allowed to come to room temperature and thionyl chloride (7.2 g, 60 mmoles) was added dropwise. The mixture was allowed to stir one hour at room temperature. The solution was slowly heated to 85¡ã C. and was maintained at that temperature for 1 hour. The solution was allowed to cool to 40¡ã C. Toluene (25 ml) was added to the solution, which was then poured into a mixture of ice and water (50 ml). Another 25 ml aliquot of toluene was added. The mixture was stirred for 10 minutes to dissolve any solids and the layers were separated. The aqueous layer was extracted with toluene (3*25 ml). The combined toluene layers were washed with water and dried over magnesium sulfate. The magnesium sulfate was removed and washed with toluene. The toluene was removed under vacuum, leaving 10.0 g of the title product (91.7percent yield). Nuclear magnetic resonance assays confirmed the identity of the title compound. FDMS (MeOH) m/e 218 (M+). Analysis for C8 H7 ClO3 S: Theory: C, 43.94; H, 3.23. Found: C, 44.14; H, 3.24., 496-16-2

The synthetic route of 496-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Eli Lilly and Company; US5387681; (1995); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem