反応 #2123925

反応方程式

5-bromo-2-nitrophenol

benzyl bromide

potassium carbonate

→

2-(benzyloxy)-4-bromo-1-nitrobenzene

収率 97.0%

溶媒

acetone

反応条件

後処理

1. 1
   温度heated
2. 2
   温度to reflux for 5 h
3. 3
   濃縮the reaction mixture was concentrated in vacuo
4. 4
   workup.ADDITIONdiluted with water
5. 5
   抽出extracted with ethyl acetate
6. 6
   洗浄The organic layer was washed with brine
7. 7
   乾燥dried over sodium sulfate
8. 8
   濃縮concentrated in vacuo
9. 9
   その他The crude material was purified by flash column chromatography (9:1 hexanes/ethyl acetate)

実験手順

A mixture of 5-bromo-2-nitrophenol (10.4 g, 47.7 mmol), benzyl bromide (9.8 g, 57.2 mmol) and potassium carbonate (9.9 g, 71.5 mmol) was taken up in acetone (50 mL) and heated to reflux for 5 h. After cooling to ambient temperature, the reaction mixture was concentrated in vacuo, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography (9:1 hexanes/ethyl acetate) to give 2-(benzyloxy)-4-bromo-1-nitrobenzene (14.19 g, 97%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.76 (d, J=8.4 Hz, 1H), 7.32-7.48 (m, 5H), 7.30 (d, J=1.8 Hz, 1H), 7.19 (dd, J=8.7, 1.8 Hz, 1H), 5.23 (s, 2H).

出典