반응 #531807

반응 방정식

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

5-Benzyloxy-2-bromo-4-methoxyphenol

NaH

CH3I

→

4

수율 88.0%

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

수율 88.0%

용매

water

반응 조건

후처리

1. 1
   기타flushed 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
   온도After cooling the reaction mixture in an ice bath
5. 5
   추출The mixture was extracted with ethyl acetate
6. 6
   기타dried
7. 7
   농축concentrated
8. 8
   기타to give yellow oil that
9. 9
   기타The oil was purified by silica gel chromatography

실험 절차

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).

출처