Related Products of 2338-54-7, These common heterocyclic compound, 2338-54-7, name is 4-Fluoro-3-methylanisole, 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.
To a vigorously stirred mixture [OF 4-FLUORO-3-METHYLANISOLE] (12.0 g, 85.6 mmol) and pyri- dine (41.7 g, 527 mmol) in water (170 mL) at [50C] was added portion-wise potassium per- manganate (44.65 g, mmol) and then maintained at this temperature for 2 h. The resulting mixture was then allowed to cool to RT and allowed to stand overnight and then heated for a further 5 h at [50C.] Then the mixture was filtered over celite and then the residue was washed with sulfuric acid (conc. 100 mL). The combined filtrates were then [HALF-EVAPORA-] ted and neutralised with potasssium carbonate. Then the mixture was washed with diethyl ether and then the aqueous layer was acidified with hydrochloric acid (conc.) and the pro- duct extracted with diethyl ether. The combined extracts were then dried over sodium sul- phate. After filtration and evaporation the crude solid was [RECRYSTALLISED] from 1,2,-di- chloroethane to afford the title compound (4.4 g, 30%) as a light pink solid. MS [M/E =] 168.9 (M-H). Alternatively, a solution of 4-fluoroanisole (500 mg, 4.0 mmol) in THF (10 mL) was added to a cooled [SOLUTION (-78C) OF 2,] 2,6, 6-tetramethylpiperidine (1.1 g, 7.9 mmol) and BuLi (5 mL, 1.6 M in hexanes, 7.9 mmol) in THF (10 mL) at a slow rate to maintain the tempera- ture [BELOW-70C.] The mixture was maintained at this temperature for 12 h, and then dry C02 gas was passed into the solution. The resulting mixture was allowed to warm up to 0C and then HCl (1 M, 10 mL) was added and the product was extracted with diethyl ether. The combined organic extracts were then dried over sodium sulfate, washed with water and brine, filtered and evaporated. The crude solid was then partioned between sodium hydroxide [(1] M, 10 mL) and diethyl ether. The aqueous phase was then acidified with HCl (1 M) and the product extracted with diethyl ether. Evaporation afforded the title compound (268 mg, 40%) as a white solid. MS m/e = 168.9 (M-H).
Statistics shows that 4-Fluoro-3-methylanisole is playing an increasingly important role. we look forward to future research findings about 2338-54-7.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/14856; (2004); A1;,
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