1-(BENZYLOXY)-4-BROMO-2,5-DIMETHOXYBENZENE synthesis

4synthesis methods

Product Name:1-(BENZYLOXY)-4-BROMO-2,5-DIMETHOXYBENZENE
CAS Number:524713-43-7
Molecular formula:C15H15BrO3
Molecular Weight:323.18

74-88-4
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1-(BENZYLOXY)-4-BROMO-2,5-DIMETHOXYBENZENE

524713-43-7
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Yield:524713-43-7 88%

Reaction Conditions:

Stage #1: 5-benzyloxy-2-bromo-4-methoxyphenolwith sodium hydride in tetrahydrofuran at 0; for 0.333333 h;
Stage #2: methyl iodide in tetrahydrofuran at 20; for 18 h;

Steps:

2

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 (11H, s, ArH), 7.07 (1H, s, ArH), 7.32-7.42 (5H, m, CH₂Ph).

References:

US2006/257337,2006,A1 Location in patent:Page/Page column 17