反応 #480775

反応方程式

sodium nitrite

5-benzyloxy-2-fluoro-4-methylaniline

→

5-benzyloxy-2-fluoro-4-methylphenol

収率 27.0%

溶媒

water

water

acetic acid

sulphuric acid

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe mixture was stirred for 3 hours
3. 3
   抽出then extracted with ethyl acetate
4. 4
   洗浄The organic layer was washed with water, brine
5. 5
   乾燥dried (MgSO4)
6. 6
   その他the solvent removed by evaporation
7. 7
   その他The residue was purified by column chromatography
8. 8
   洗浄eluting with petroleum ether/ether (85/15)

実験手順

A solution of sodium nitrite (1.68 g, 24 mmol) in water (3.5 ml) was added to a solution of 5-benzyloxy-2-fluoro-4-methylaniline (4.7 g, 20 mmol) in acetic acid (25 ml) and 70% sulphuric acid (25 ml) at 10° C. The mixture was stirred at 10° C. for 20 minutes and a solution of copper(II)nitrate trihydrate (481 g, 2 mol) in water (790 ml) followed by copper(II)oxide (3 g, 19 mmol) was added. The mixture was stirred for 3 hours then extracted with ethyl acetate. The organic layer was washed with water, brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with petroleum ether/ether (85/15) to give 5-benzyloxy-2-fluoro-4-methylphenol (1.25 g, 27%) as an orange oil.

出典