Category: 934240-59-2

Synthetic Route of 934240-59-2, These common heterocyclic compound, 934240-59-2, name is 1-((4-Bromophenoxy)methyl)-2-fluorobenzene, 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.

Description 2j Methyl (2SV2-r(te/f-butoxycarbonvnaminol-5-f4-r(2- fluorobenzyl)oxylphenyl)-5-oxopentanoate (D2)To a stirred suspension of magnesium metal (9Og) in dry THF (60OmL) under a nitrogen atmosphere at room temperature was added iodine (0.3g). The mixture was heated to an internal temperature of 63-65C. A solution of 1-[(4- bromophenoxy)methyl]-2-fluorobenzene (D1 , 693g) in THF (150OmL) was added in two batches, firstly 45 mL was added in one go. Secondly, the remaining solution (1500 mL) was added dropwise. After addition, the reaction was heated at reflux for 1 h. The reaction mixture was cooled to room temperature. This reaction mixture was then added slowly to a solution of 1-te/f-butyl 2-methyl (2S)-5-oxopyrrolidine-1 ,2- dicarboxylate (ISOCHEM, 30Og) in THF (150OmL) cooled to -6OC, maintaining the internal temperature below -60C. The addition was completed in 1.25 hours. The reaction mixture was stirred for a further 1 hour after addition, lsopropyl alcohol (30OmL) was then added drop-wise whilst maintaining the temperature below -60C. A mixture of aqueous saturated ammonium chloride solution/aqueous saturated sodium chloride solution (2/1 ; 90OmL) was added whilst maintaining the temperature at -50C. Water (600 mL) was added to dissolve the yellow precipitate. The organic phase was separated and was washed with aqueous 13% NaCI solution (60OmL). The organic phase was concentrated to dryness. EtOAc (150OmL) was then added and the solution was evaporated under reduced pressure to remove water. The residue was purified by chromatography on silica gel eluting with cyclohexane / ethyl acetate (95:5 to 8:2) to afford the title compound (287 g); 1H NMR (600 MHz, DMSO- d6) ?(ppm): 7.93 (d, 2H); 7.57 (td, 1 H); 7.44 (m, 1 H); 7.27 (m, 3H); 7.14 (d, 2H); 5.24 (s, 2H); 4.04 (m, 1 H); 3.61 (s, 3H); 3.03 (m, 2H); 1.94 (m, 2H); 1.38 (s, 9H).

The synthetic route of 934240-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/122546; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 934240-59-2, 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 934240-59-2 as follows.

To a mixture of magnesium turnings (12.79g. 533mol), a trace of iodine and 1 ,2-dibromoethane in THF (86.ml)at 70-750C, a solution of (4-bromophenyl (2- fluorophenyl)methyl ether) (100g, 355.6mmol) in THF (216.25ml) was added over about 2 hours. The mixture was heated for a further 2 hours at 70-75C then cooled to room temperature to give a solution of the Grignard reagent. A solution of 1-(1 ,1-dimethylethyl) 2-methyl (2S)-5-oxo-1 ,2-pyrrolidinedicarboxylate (43.25g, 177.8mmol) in THF (216.25ml) was cooled to -600C and the solution of the Grignard reagent was added over 1 hour, then the mixture was stirred for 3 hours at -60C. lsopropanol (43.25ml) was added dropwise, followed by saturated aqueous ammonium chloride (86.5ml) and brine (43.25ml), then the mixture warmed to room temperature. Water (173ml) and 50% acetic acid (50ml) to pH 6- 7, followed by ethyl acetate (129.7ml). The layers were separated and the aqueous extracted with ethyl acetate (2 x 129.7ml). The combined organic layers were washed with brine then concentrated under vacuum. The residue was stirred with hexane (216.2ml), then the solid was filtered and washed with hexane. To the resulting solid, isopropanol (432.5ml) was added and the mixture stirred at 45C for 15 minutes, then cooled to 5- 100C and stirred for 2 hours. The solid was filtered, washed with isopropanol and dried to give the title compound as a solid.1 H NMR (300 MHz, CHCI3-d): delta(ppm): 1.42 (s, 9H); 2.04 (m, 1 H); 2.28 (m, 1 H); 3.03 (m, 2H); 3.74 (s, 3H); 4.37 (m, 1 H); 5.19 (b, 1 H); 5.20 (s, 2H); 7.02 (d, 2H); 7.1 1 (t, 1 H); 7.17 (t, 1 H); 7.33 (m, 1 H); 7.48 (t, 1 H); 7.94 (d, 2H).

According to the analysis of related databases, 934240-59-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/90114; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

934240-59-2, name is 1-((4-Bromophenoxy)methyl)-2-fluorobenzene, 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. Recommanded Product: 934240-59-2

To a stirred suspension of magnesium metal (9Og) in dry THF (60OmL) under a nitrogen atmosphere at room temperature was added iodine (0.3g). The mixture was heated to an internal temperature of 64 +/- 2C. A solution of 1-[(4- bromophenoxy)methyl]-2-fluorobenzene (693g) in THF (150OmL) was added in two batches. Firstly 45 mL was added. Secondly, the remaining solution (1455 mL) was added dropwise. After addition, the reaction was heated at reflux for 1 h. The reaction mixture was cooled to room temperature. This reaction mixture was then added slowly to a solution of commercially available 1-te/t-butyl 2-methyl (2S)-5-oxopyrrolidine-1 ,2- dicarboxylate (30Og) in THF (150OmL) cooled to -6O0C, maintaining the internal temperature below -600C. The addition was completed in 2 hours. The reaction mixture was stirred for a further 15 minutes after addition, lsopropyl alcohol (30OmL) was then added dropwise whilst maintaining the temperature below -600C. A mixture of aqueous saturated ammonium chloride solution/aqueous saturated sodium chloride solution (2/1 ; 90OmL) was added whilst maintaining the temperature at -500C. Water (600 ml.) was added to dissolve the yellow precipitate. The organic phase was separated and was washed with aqueous 13% NaCI solution (60OmL). The organic phase was concentrated to dryness. EtOAc (150OmL) was then added and the solution was evaporated under reduced pressure to remove water. The residue was purified by chromatography on silica gel eluting with cyclohexane / ethyl acetate (90:10 to 8:2) to afford the title compound (287 g); 1H NMR (600 MHz, DMSO-d6) delta(ppm): 7.93 (d, 2H); 7.57 (td, 1 H); 7.44 (m, 1 H); 7.27 (m, 3H); 7.14 (d, 2H); 5.24 (s, 2H); 4.04 (m, 1 H); 3.61 (s, 3H); 3.03 (m, 2H); 1.94 (m, 2H); 1.38 (s, 9H).

The synthetic route of 934240-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/90114; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem