反応 #1797507

反応方程式

Water

3-Bromophenol

sodium nitrate

water

→

title compound

収率 20.0%

5-bromo-2-nitrophenol

収率 20.0%

溶媒

sulfuric acid

反応条件

後処理

1. 1
   抽出the resulting mixture was extracted with diethyl ether
2. 2
   乾燥the extract was dried (MgSO4)
3. 3
   ろ過filtered
4. 4
   濃縮concentrated
5. 5
   その他The residue was purified by flash chromatography (silica gel, 10% ethyl acetate/hexanes)

実験手順

3-Bromophenol (32.9 g, 0.19 mol) was added slowly to a cold (10° C.) solution of sodium nitrate (29.0 g, 0.34 mol) in conc. sulfuric acid; (40.0 g) and water (70.0 mL) and the resulting mixture was allowed to stir at room temperature for 2 h. Water (200 mL) was added and the resulting mixture was extracted with diethyl ether and the extract was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (silica gel, 10% ethyl acetate/hexanes) to afford first the title compound (8.1 g, 20%), mp 40-42° C., then the undesired isomer, 3-bromo-4-nitrophenol, as a yellow solid (12.7 g, 31%). mp 125-127° C.

出典