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

4-BROMO-2-ETHOXY-1-METHOXYBENZENE synthesis

6synthesis methods

Product Name:4-BROMO-2-ETHOXY-1-METHOXYBENZENE
CAS Number:52849-52-2
Molecular formula:C9H11BrO2
Molecular Weight:231.09

37942-01-1 Synthesis

37942-01-1
245 suppliers
$6.00/5g

75-03-6
354 suppliers
$11.00/5g

52849-52-2
39 suppliers
$45.00/100mg

Yield:52849-52-2 100%

Reaction Conditions:

with potassium carbonate in tetrahydrofuran at 20; for 10.5 h;

Steps:

Application of Synthesis

The first part of the application of synthesis was to synthesize the nucleophilic boronic acids, as shown in the reaction scheme below: (0110) (0111) The hydroxyl group of the 2-methoxyphenol was first acetylated to lower the ability of electrophilic aromatic substitution on 4-position, avoiding the formation of by-products. N-bromosuccinimide (NBS) was then used to selectively conjugate the bromine atom on the 3-position through bromination, followed by hydrolysis of the acetyl group under a basic condition and reacting with diiodoethane to furnish the ethoxy compound 116. The compound 116 was reacted with n-butyl lithium (n-BuLi) and trimethyl borate to form a boronic ester. At last, the target product of boronic acid 117 was obtained through hydrolysis with hydrogen chloride. (0112) The second part was to synthesize the sulfonyl alkyne molecular fragment, as shown in the reaction scheme below. The n-BuLi and trimethylsilylacetylene were used for deprotonation and then reacted with dimethyl sulfide through substitution reaction to furnish the compound 120, followed by treating with meta-chloroperoxybenzoic acid (m-CPBA) to oxidize the sulfide compound to furnish the compound 121. The protecting trimethylsilyl group was removed from the compound 121 through the acid property of silica gel to produce the compound 122.

References:

US11008288,2021,B1 Location in patent:Page/Page column 20-21