Category: 439814-87-6

Some common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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. COA of Formula: C9H10BrFO2

4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene (87.0 g, 349.27 mmol) was dissolved in THF (700 mL) and cooled to -78 C. n-Butyl lithium (185.42 mL of a 2.5 M soln in hexanes, 461.04 mmol) was rapidly added and immediately followed by addition of DMF (40.40 mL, 523.91 mmol). Reaction was stirred in the cold for 30 min then allowed to warm to rt and stirred for 1 h. The reaction solution was diluted with H2O (500 mL) and extracted with Et2O (3*500 mL). The combined organic extracts were washed with brine (3*200 mL), dried (Na2SO4), filtered, concentrated and chromatographed (eluted with 10% EtOAc in hexanes) to provide 45.90 g of 4-(dimethoxymethyl)-3-fluorobenzaldehyde as a clear oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 439814-87-6, its application will become more common.

Reference:
Patent; Pfizer Inc; US2006/58361; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 439814-87-6,Some common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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.

To a solution of 4-bromo-1-dimethoxymethyl-2-fluorobenzene (4.53 g, 18.2 mmol) in tetrahydrofuran (50 mL) were added n-butyllithium (1.6 mol/L in hexanes; 15 mL) and dimethylformamide (2.1 mL, 27 mmol) sequentially at -78 C. under nitrogen atmosphere, and the mixture was stirred for 15 min. Water was added, and the mixture was extracted twice with ether. The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (6:1 Hexane/ethyl acetate) to afford 4-dimethoxymethyl-3-fluorobenzaldehyde (2.26 g, 63%). 1H NMR (400 MHz, CDCl3) delta (ppm) 3.36 (s, 6H), 5.61 (s, 1H), 7.53 (dd, J=9.8, 1.6 Hz, 1H), 7.65 (dd, J=7.8, 1.6 Hz, 1H), 7.73 (t, J=7.8 Hz, 1H), 9.95 (d, J=2.0 Hz, 1H).

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-(dimethoxymethyl)-2-fluorobenzene, its application will become more common.

Reference:
Patent; Akama, Tsutomu; Holcomb, Ryan; Tolman, Richard L.; US2002/120144; (2002); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 439814-87-6,Some common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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.

To a solution of 4-bromo-1-dimethoxymethyl-2-fluorobenzene (4.53 g, 18.2 mmol) in tetrahydrofuran (50 mL) were added n-butyllithium (1.6 mol/L in hexanes; 15 mL) and dimethylformamide (2.1 mL, 27 mmol) sequentially at -78 C. under nitrogen atmosphere, and the mixture was stirred for 15 min. Water was added, and the mixture was extracted twice with ether. The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (6:1 Hexane/ethyl acetate) to afford 4-dimethoxymethyl-3-fluorobenzaldehyde (2.26 g, 63%). 1H NMR (400 MHz, CDCl3) delta (ppm) 3.36 (s, 6H), 5.61 (s, 1H), 7.53 (dd, J=9.8, 1.6 Hz, 1H), 7.65 (dd, J=7.8, 1.6 Hz, 1H), 7.73 (t, J=7.8 Hz, 1H), 9.95 (d, J=2.0 Hz, 1H).

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-(dimethoxymethyl)-2-fluorobenzene, its application will become more common.

Reference:
Patent; Akama, Tsutomu; Holcomb, Ryan; Tolman, Richard L.; US2002/120144; (2002); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 439814-87-6, A common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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.

Step 2 4-(4-Acetylpiperazin-l-yl)-2-fluorobenzaldehyde Palladium(II) acetate (111 mg, 0.49 mmol), 2-dicyclohexylphosphino-2′,6′-di-i-propoxy- Iota,Gamma-biphenyl (469 mg, 0.98 mmol) and sodium teri-butoxide (4.88 g, 49.2 mmol) were combined and the flask was purged with nitrogen. A solution of 1-piperazin-l-ylethanone (4.1 g, 32 mmol) and 4-bromo-l-(dimethoxymethyl)-2-fluoro-benzene (6.13 g, 24.6 mmol) in 1,4-dioxane (82 mL) was then added and the reaction was stirred at 100 C for 16 hours. The reaction was then filtered through diatomaceous earth and concentrated. The resulting residue was dissolved in 50 mL of THF and 50 mL of 1 N aqueous HC1 was added and the reaction was stirred at ambient temperature for 16 hours. The reaction was then neutralized with saturated aqueous Na2C03 and extracted with dichloromethane (x3), dried with MgSC>4, concentrated and purified by silica gel column chromatography (0-10% methanol in dichloromethane) to give 4-(4-acetylpiperazin-l-yl)-2-fluoro- benzaldehyde (3.68 g, 60% yield). LCMS (m/z) ES+251 [M+l]+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FAUBER, Benjamin; RENE, Olivier; WO2013/92941; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 439814-87-6, name is 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene, molecular formula is C9H10BrFO2, 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. name: 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene

4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene (87.0 g, 349.27 mmol) was dissolved in THF (700 mL) and cooled to -78 C. n-Butyl lithium (185.42 mL of a 2.5 M soln in hexanes, 461.04 mmol) was rapidly added and immediately followed by addition of DMF (40.40 mL, 523.91 mmol). Reaction was stirred in the cold for 30 min then allowed to warm to rt and stirred for 1 h. The reaction solution was diluted with H2O (500 mL) and extracted with Et2O (3*500 mL). The combined organic extracts were washed with brine (3*200 mL), dried (Na2SO4), filtered, concentrated and chromatographed (eluted with 10% EtOAc in hexanes) to provide 45.90 g of 4-(dimethoxymethyl)-3-fluorobenzaldehyde as a clear oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 439814-87-6, its application will become more common.

Reference:
Patent; Pfizer Inc; US2006/58361; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem