反応 #531807

反応方程式

5-Benzyloxy-2-bromo-4-methoxy-phenol

5-Benzyloxy-2-bromo-4-methoxyphenol

NaH

CH3I

→

4

収率 88.0%

1-Benzyloxy-4-bromo-2,5-dimethoxybenzene

収率 88.0%

溶媒

water

反応条件

後処理

1. 1
   その他flushed with Ar
2. 2
   workup.ADDITIONDry THF (50 mL) was added
3. 3
   workup.STIRRINGthe mixture stirred at room temperature under Ar for 18 h
4. 4
   温度After cooling the reaction mixture in an ice bath
5. 5
   抽出The mixture was extracted with ethyl acetate
6. 6
   その他dried
7. 7
   濃縮concentrated
8. 8
   その他to give yellow oil that
9. 9
   その他The oil was purified by silica gel chromatography

実験手順

5-Benzyloxy-2-bromo-4-methoxy-phenol 3 (2.76 g, 89.0 mmol) and NaH (0.89 g, 13.0 mmol, 60% dispersion in oil) were added to a flask and flushed with Ar. Dry THF (50 mL) was added and the suspension was stirred in an ice bath for 20 min. CH3I (1.7 mL, 27.0 mmol, filtered through basic alumina) was added and the mixture stirred at room temperature under Ar for 18 h. After cooling the reaction mixture in an ice bath, water was added slowly. The mixture was extracted with ethyl acetate, dried and concentrated to give yellow oil that solidified under vacuum. The oil was purified by silica gel chromatography using silica gel with (10% ethyl acetate/hexanes) to give 2.5 g (88%) of 4 as a white solid. 1H-NMR (400 MHz, CDCl3) dH 3.75 (3H, s, OCH3), 3.84 (3H, s, OCH3), 5.15 (2H, s, CH2Ph), 6.57 (1H, s, ArH), 7.07(1H,s,ArH), 7.32-7.42(5H,m,CH2Ph).

出典