反応 #7591

反応方程式

5-benzyloxy-2-fluoro-4-methylaniline

sodium nitrite

→

5-benzyloxy-2-fluoro-4-methylphenol

収率 27.0%

溶媒

acetic acid

sulphuric acid

water

water

反応条件

後処理

1. 1
   workup.STIRRINGAfter stirring for 3 hours
2. 2
   抽出the mixture was extracted with ethyl acetate
3. 3
   洗浄The organic layer was washed with water
4. 4
   乾燥brine, dried (MgSO4)
5. 5
   その他the solvent evaporated
6. 6
   その他The resulting oil was purified by flash chromatography

実験手順

The starting material 5-benzyloxy-2-fluoro-4-methylphenol, was obtained by adding a solution of sodium nitrite (1.68 g, 24mmol) in water (3.5 ml), dropwise, to a solution of 5-benzyloxy-2-fluoro-4-methylaniline (4.7 g, 20 mmol) in acetic acid (82 ml) and 70% sulphuric acid (3.15 ml) cooled at 10° C. The mixture was stirred vigorously for 20 minutes, then a solution of copper(II)nitrate trihydrate (481 g, 2 mol) in water (790 ml) was added, followed by copper(II)oxide (3 g, 19 mmol). After stirring for 3 hours, the mixture was extracted with ethyl acetate. The organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated. The resulting oil was purified by flash chromatography using petroleum ether/ether (85/15) as eluent to give 5-benzyloxy-2-fluoro-4-methylphenol as an orange oil (1.25 g, 27%).

出典