ChemicalBook CAS DataBase List 4-BROMO-2-ISOPROPOXY-1-METHOXYBENZENE

4-BROMO-2-ISOPROPOXY-1-METHOXYBENZENE synthesis

5synthesis methods

Product Name:4-BROMO-2-ISOPROPOXY-1-METHOXYBENZENE
CAS Number:462092-23-5
Molecular formula:C10H13BrO2
Molecular Weight:245.11

37942-01-1 Synthesis

37942-01-1
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$6.00/5g

75-26-3
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462092-23-5
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$55.00/250mg

Yield:462092-23-5 98%

Reaction Conditions:

Stage #1: 5-bromo-2-methoxyphenolwith potassium carbonate in N,N-dimethyl-formamide; for 0.166667 h;Inert atmosphere;
Stage #2: isopropyl bromide in N,N-dimethyl-formamide at 80; for 20 h;Inert atmosphere;

Steps:

4-Bromo-2-isopropoxy-1-methoxybenzene

To a solution of 5-bromo-2-methoxyphenol (5.0 g, 24.63 mmol) in DMF (40 mL) was added K2CO3 (10.19 g, 73.89 mmol) and resultant solution was stirred for 10 min. 2-Bromopropane (5.78 mL, 61.56 mmol) was added and then the mixture was heated at 80 °C for 20 h. The residue was diluted with ethyl acetate (30 mL) and water (30 mL) and the organic layer was separated. The aqueous mixture was further extracted with ethyl acetate (3 × 50 mL) and the combined organic extracts were washed with water (3 × 50 mL), dried (MgSO4) and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (9:1 n-hexanes, ethyl acetate) to give the title compound (5.93 g, 98 %) as a white solid.

References:

Jung, Eun-Kyung;Leung, Euphemia;Barker, David [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 13,p. 3001 - 3005] Location in patent:supporting information