反应详情

温度

110 °C

A solution of 4-fluoro-2-nitrobenzoic acid (1.81 g) in butanol (20 ml) was mixed with sulfuric acid (3 ml) and stirred at 110° C. for 4 hours. Ethyl acetate (100 ml) was added, and the mixture was washed with saturated sodium bicarbonate solution (3×50 ml), dried with sodium sulfate, filtered and concentrated in vacuo. The residue (2.2 g) was added dropwise at −10° C. to a sodium butoxylate solution prepared from butanol (20 ml) and sodium hydride (2.18 g) at −10° C. under argon and then stirred for 20 hours. Ethyl acetate (100 ml) was added, and the mixture was washed with water (2×50 ml), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by preparative HPLC. The butyl 4-butoxy-2-nitrobenzoate was hydrolyzed with sodium hydoxide (5N; 100 ml) in ethanol at room temperature for 3 hours. The mixture was acidified with hydrochloric acid (10N; 100 ml) and extracted with dichloromethane, and the organic phase was dried over sodium sulfate, filtered and concentrated. This resulted in the product with the molecular weight of 239.23 (C11H13NO5); MS (ESI): 240 (M+H+).

1. washthe mixture was washed with saturated sodium bicarbonate solution (3×50 ml)
2. dry with materialdried with sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. additionThe residue (2.2 g) was added dropwise at −10° C. to a sodium butoxylate solution
6. customprepared from butanol (20 ml) and sodium hydride (2.18 g) at −10° C. under argon
7. stirringstirred for 20 hours
8. washthe mixture was washed with water (2×50 ml)
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was purified by preparative HPLC
13. waitThe butyl 4-butoxy-2-nitrobenzoate was hydrolyzed with sodium hydoxide (5N; 100 ml) in ethanol at room temperature for 3 hours
14. extractionextracted with dichloromethane
15. dry with materialthe organic phase was dried over sodium sulfate
16. filtrationfiltered
17. concentrationconcentrated
18. customThis resulted in the product with the molecular weight of 239.23 (C11H13NO5)