Reference of 437-83-2,Some common heterocyclic compound, 437-83-2, name is 3-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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.
Hydrobromic acid (48% in water, 140 mL) is added slowly to an aliquot of 11 (14. 33 g, 101. 5 mmol) cooled to 0 C. The resulting solid is broken up with a glass rod and stirred vigorously at 0 C for 10 min. A solution of sodium nitrite (7. 40g, 107. 2 mmol) in water (50 mL) is added slowly (-1. 5 h) to the stirred slurry containing 3-fluoro-2- methoxyphenylamine and hydrobromic acid, maintaining the temperature of the reaction mixture below 5 C. A purple solution of cuprous bromide (9. 62 g, 67. 1 mmol) in hydrobromic acid (48% in water, 50 mL) is added dropwise to the reaction mixture, maintaining the temperature of the reaction mixture below 5 C. The resulting reaction mixture is heated at 60 C until the evolution of gas ceases (-2. 5 h). The reaction mixture is cooled to room temperature, and the product extracted with diethyl ether (6 x 150 mL). The combined organic extracts are washed with brine (3 x 150 mL), dried over magnesium sulfate, and evaporated under reduced pressure to give 1-BROMO-3-FLUORO-2-METHOXYBENZENE as a brown oil. This product is of sufficient purity (295% by NMR spectroscopy) to use directly in the next synthetic STEP. 1H NMR (CDCl3) : No.3. 95 (d, JH-F= 1.5 Hz, 3H, OCH3), 6. 88 (apparent t OF D, JH-H = 8. 0 Hz, JH-F = 5. 5 Hz, 1H, H-5), 7. 04 (ddd, JH-F = 10. 5 Hz, JH-H = 8. 0 HZ, JH-H = 1. 5 Hz, 1H, H-4), 7. 30 (d of apparent T, JH-H = 8. 0 Hz, JH-H = 1. 5 Hz, JH-F = 1. 5 Hz, 1H, H-6). I9F {LH} NMR (CDCl3) : S-127. 7 (s). 13C {IH} NMR (CDCl3) : 1561. 4 (d, JC-F= 5. 0 Hz, OCH3), 116. 2 (d, JC-F = 19. 5 Hz, C-4), 117. 7 (D, JC-F = 3. 0 Hz, C-1), 124. 5 (d, JC-F = 8. 0 Hz, C-5), 128. 5 (D, JC-F = 3. 5 Hz, C-6), 145. 7 (d, Jc-F = 12. 5 Hz, C-2), 156. 2 (d, JC-F = 250. 5 Hz, C-3).
The synthetic route of 437-83-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WO2005/19228; (2005); A1;,
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