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ChemicalBook CAS DataBase List 1-(benzyloxy)-4-bromo-2-methylbenzene

1-(benzyloxy)-4-bromo-2-methylbenzene synthesis

2synthesis methods
-

Yield:338454-32-3 99%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20; for 72 h;

Steps:

107.1 Step 1 : l-(Benzyloxy)-4-bromo-2-methylbenzene

Example 107 (E)-3 -(4-(6-hvdroxy-2-(4-isobutyl-3 -methylphenyl)- 1 -methyl- 1.2.3.4-tetrahydroisoquinolin- 1 - vDphenvDacrylic acid: Step 1 : l-(Benzyloxy)-4-bromo-2-methylbenzene: 4-Bromo-2-methylphenol (0.5 g, 2.67 mmol) was dissolved in dimethy If orm amide (5.35 ml). Potassium carbonate (0.739 g, 5.35 mmol) was added followed by benzyl bromide (0.350 ml, 2.94 mmol). The reaction was stirred at rt for 72 h. The reaction was quenched with water and extracted with dichloromethane three times. The organic layers were combined, passed through a phase separator and concentrated. The crude material was purfied by silica gel chromatography (0-30% ethyl acetate/heptanes) to afford product (732 mg, 2.64 mmol, 99 % yield) as a clear oil. NMR (400 MHz, Chloroform-d) δ 7.49 - 7.32 (m, 5H), 7.31 (dd, J = 2.6, 0.9 Hz, 1H), 7.26 (ddd, J = 8.6, 2.5, 0.7 Hz, 1H), 6.77 (d, J = 8.6 Hz, 1H), 5.08 (s, 2H), 2.28 (s, 3H).

References:

WO2015/92634,2015,A1 Location in patent:Paragraph 00481