反应详情

温度

90 °C

3-Fluoromethyl aniline (containing 37% 3-methylaniline, 13.6 g≡68 mmol) was mixed with dry acetonitrite (10 ml), sodium bicarbonate (15.4 g, 183 mmol) and methyl chloroacetate (12 ml, 137 mmol) and heated to 90° C. under nitrogen for 14 h. The cooled reaction mixture was poured into water (100 ml) and extracted with ethyl acetate (4×100 ml). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give an orange oil. The crude product was purified by chromatography on silica (Merck 9385, 1.5 kg) eluted with ether-hexane 1:4 to give Intermediate 54 (6.45 g, 48%) as a white crystalline solid, m.p. 47°-47.5°.

1. customThe cooled reaction mixture
2. extractionextracted with ethyl acetate (4×100 ml)
3. dry with materialThe combined organic extracts were dried (Na2SO4)
4. concentrationconcentrated in vacuo
5. customto give an orange oil
6. customThe crude product was purified by chromatography on silica (Merck 9385, 1.5 kg)
7. washeluted with ether-hexane 1:4