تفاعل #531807

معادلة التفاعل

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

5-Benzyloxy-2-bromo-4-methoxyphenol

NaH

CH3I

→

4

المردود 88.0%

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

المردود 88.0%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   أخرىflushed 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
   درجة الحرارةAfter cooling the reaction mixture in an ice bath
5. 5
   استخلاصThe mixture was extracted with ethyl acetate
6. 6
   أخرىdried
7. 7
   تركيزconcentrated
8. 8
   أخرىto give yellow oil that
9. 9
   أخرىThe oil was purified by silica gel chromatography

الإجراء التجريبي

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).

المصدر