Category: 2859-78-1

2859-78-1, A common heterocyclic compound, 2859-78-1, name is 4-Bromo-1,2-dimethoxybenzene, molecular formula is C8H9BrO2, 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.

METHOD AThe synthesis of (i?)-l-(3,4-dimethoxyphenyl)-3-methylpiperazine.HCl is a representative example of the general two step method of making secondary amine building blocks of the type (V) using a palladium coupling reaction. (R)-tert-bntyl 4-(3,4-dimethoxyphenyl)-2-methylpiperazine-l-carboxylate Palladium(II) acetate (0.052 g, 0.230 mmol) and (R)-(+)-2,2′-bis(diphenylphosphino)-l,l?- binaphthyl (0.115 g, 0.180 mmol) were added to 4-bromoveratrole (0.662 mL, 4.61 mmol), (R)–N-boc-2 -methyl piperazine (0.923 g, 4.61 mmol) and sodium tert-butoxide (0.664 g, 6.91 mmol) in anhydrous toluene (12 mL) under argon. The resulting solution was stirred at reflux for 16 hours. The reaction mixture was diluted with Et2O and filtered through celite. The resulting mixture was evaporated to dryness to afford crude (R)-tert-butyl 4- (3,4-dimethoxyphenyl)-2-methylpiperazine-l-carboxylate. The crude product was purified by flash silica chromatography, elution gradient 0 to 25% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford (R)-tert-butyl 4-(3,4-dimethoxyphenyl)-2- methylpiperazine-1-carboxylate (0.871 g, 56.2 %) as a beige solid. MS (+ve ESI) : Rt = 2.57 min, 337.31 (M+H)+1H NMi? (400.132 MHz, CDC13) delta 1.33 (3H, d), 1.49 (9H, s), 2.67 (IH, m), 2.85 (IH, m), 3.24 (2H, m), 3.37 (IH, d), 3.84 (3H, s), 3.88 (3H, s), 3.94 (IH, m), 4.34 (IH, s), 6.43 (IH, m), 6.54 (IH, d), 6.79 (IH, d)(R)-l-(3,4-dimethoxyphenyl)-3-methylpiperazine.HCl(R)-tert-buty{ 4-(3,4-dimethoxyphenyl)-2-methylpiperazine-l-carboxylate (0.400 g, 1.19 mmol) was added to hydrochloric acid in methanol (methanol reagent 10) (15 mL, 1.19 mmol) and the resulting solution was stirred at room temperature for 16 hours. The resulting mixture was evaporated to dryness and the residue was azeotroped with DCM to afford crude (i?)-l-(3,4-dimethoxyphenyl)-3-methylpiperazine (100 %). MS (+ve ESI) : Rt = 1.22 min, 237.30 (M+H)+

The synthetic route of 2859-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/1127; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

2859-78-1, name is 4-Bromo-1,2-dimethoxybenzene, belongs to ethers-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. 2859-78-1

General procedure: To a solution of 4-bromoanisole (200.8 mg, 1.09 mmol, 1.0 equiv) in acetonitrile (2 mL) was added N-chlorosuccinimide(NCS) (158.3 mg, 1.19 mmol, 1.1 equiv) at rt to give a slightly cloudy mixture. Chlorotrimethylsilane (TMSCl) (14 muL, 0.11 mmol, 0.1 equiv) was then added drop-wise to the reaction mixture. Within a few minutes, the reaction mixture became clear pale yellow solution. The mixture continued to stir at rt for 1 h and was diluted with hexane. The biphasic mixture was concentrated on a rotary evaporator to a crude white solid-oil mixture. This mixture was taken up in hexane and filtered through a short plug of SiO2 and eluted with 5-10% EtOAc-hexane solution. The clear filtrate was concentrated to obtain a mixture of 4-bromo-2-chloro-1-methoxybenzene (2a-Cl) and 2,4-dichloro-1-methoxybenzene (2a-diCl) 237.0 mg (88% of 2a-Cl and 11% of 2a-diCl,based on NMR ratio 2a-Cl: 2a-diCl = 7.1: 1.0; as a pale yellow solid).

Statistics shows that 2859-78-1 is playing an increasingly important role. we look forward to future research findings about 4-Bromo-1,2-dimethoxybenzene.

Reference:
Article; Maibunkaew, Tapanee; Thongsornkleeb, Charnsak; Tummatorn, Jumreang; Bunrit, Anon; Ruchirawat, Somsak; Synlett; vol. 25; 12; (2014); p. 1769 – 1775;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem