Reaction #531807

Reaction equation

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

5-Benzyloxy-2-bromo-4-methoxyphenol

NaH

CH3I

→

4

Yield 88.0%

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

Yield 88.0%

Solvents

water

Conditions

Workup

1. 1
   Otherflushed 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
   TemperatureAfter cooling the reaction mixture in an ice bath
5. 5
   ExtractionThe mixture was extracted with ethyl acetate
6. 6
   Otherdried
7. 7
   Concentrationconcentrated
8. 8
   Otherto give yellow oil that
9. 9
   OtherThe oil was purified by silica gel chromatography

Procedure

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).

Source