These common heterocyclic compound, 349-60-0, name is 1-Methoxy-3,5-bis(trifluoromethyl)benzene, 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. HPLC of Formula: C9H6F6O
3,5-Bis(trifluoromethyl)anisole (5.0 g 21 mmol) and TMEDA (4.0 mL, 3.0 g,26 mmol) were dissolved in dry Et2O (60 mL), cooled to -10 0C and treated in portions with H-BuLi (2.5 M in hexanes; 10 mL, 25 mmol). The mixture was warmed to 25 0C and stirred for 90 min. The mixture was cooled to -78 0C, treated dropwise with DMF (2.3 mL, 2.2 g, 30 mmol), stirred for 30 min, warmed to 25 0C and stirred for 30 min. The reaction was quenched by addition of H2O (50 mL) and extracted with Et2O (2 x 75 mL). The combined organic fractions were washed with satd NaCl solution (30 mL), dried (Na2SO4) and evaporated. The residue was purified by silica gel chromatography to give the anisaldehyde derivative (3.3 g). This material (3.0 g, 11 mmol) was dissolved in CH2Cl2 (75 mL), cooled to -78 0C and treated with BBr3 (1 M solution in CH2Cl2; 12 mL, 12 mmol). The mixture was stirred for 30 min at -78 0C, warmed to 25 0C and stirred for 90 min. H2O (100 mL) was added and stirring was continued for 30 min. The separated organic phase was washed with satd NaCl solution, dried (Na2SO4) and evaporated. The residue was purified by silica gel chromatography with 0-20percent EtOAc/hexane to give the purified aldehyde (2.0 g): 1H NMR (400 MHz, CDCl3) delta 12.27 (s, IH), 10.34 (s,lH), 7.51 (s, IH); EIMS m/z 258.
The synthetic route of 1-Methoxy-3,5-bis(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; DOW AGROSCIENCES LLC; YOUNG, David; SHABER, Steven; AVILA-ADAME, Cruz; BREAUX, Nneka; RUIZ, James; SIDDALL, Thomas; WEBSTER, Jeffery; WO2010/83307; (2010); A2;,
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