3,5-Bis(octyloxy)benzyl bromide synthesis

5synthesis methods

Product Name:3,5-Bis(octyloxy)benzyl bromide
CAS Number:188011-21-4
Molecular formula:C23H39BrO2
Molecular Weight:427.46

188011-20-3
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188011-21-4
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Yield:188011-21-4 95%

Reaction Conditions:

with carbon tetrabromide;triphenylphosphine in dichloromethane at 20;Inert atmosphere;

Steps:

4.1.3. Synthesis of 1-(bromomethyl)-3,5-bis(octyloxy)benzene (7) and 1-(bromomethyl)-3,5-bis(hexadecyloxy)benzene (8)

General procedure: To a stirring solution of appropriate benzyl alcohol 5 or 6 (1 equiv) and Ph₃P (1.2 equiv), CBr₄ (1.2 equiv) was added under argon. The reaction was monitored until completion by thin layer chromatography. If the reaction was not complete after 10 min, an additional 1 equivalent of Ph₃P and CBr₄ were added. Upon completion of the reaction, water was added to the reaction mixture. The aqueous layer was extracted with ethyl acetate and the organic layer was concentrated under reduced pressure to produce the crude reaction mixture. The crude product was purified by silica gel column chromatography using ethyl acetate/hexane (10:90) as the eluent.

References:

Das, Joydip;Pany, Satyabrata;Majhi, Anjoy [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 18,p. 5321 - 5333] Location in patent:experimental part

111-83-1 Synthesis