Реакция #7592

Уравнение реакции

5-benzyloxy-2-fluoro-4-methylnitrobenzene

→

5-benzyloxy-2-fluoro-4-methylaniline

Выход 87.7%

Растворители

acetic acid

water

Условия реакции

Обработка

1. 1
   Другоеat ambient temperature
2. 2
   ТемператураThe mixture was heated
3. 3
   Температураit was cooled
4. 4
   Другоеpartitioned between ethyl acetate and water
5. 5
   ПромывкаThe organic layer was washed with water, aqueous saturated sodium carbonate solution
6. 6
   Сушкаbrine, dried (MgSO4)
7. 7
   Другоеthe solvent evaporated
8. 8
   ДругоеThe residue was purified by flash chromatography

Методика

The starting material, 5-benzyloxy-2-fluoro-4-methylaniline, was obtained by adding iron powder (2.88 g, 51 mmol), in portions, to a solution of 5-benzyloxy-2-fluoro-4-methylnitrobenzene (4.8 g, 18 mmol) in acetic acid (33 ml) and water (5.7 ml), at ambient temperature. The mixture was heated and after stirring at 100° C. for 10 minutes, it was cooled and partitioned between ethyl acetate and water. The organic layer was washed with water, aqueous saturated sodium carbonate solution and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using petroleum ether/ethyl acetate (8/2) as eluent to give 5-benzyloxy-2-fluoro-4-methylaniline (3.65 g, 87%).

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