137600-75-0Relevant academic research and scientific papers
Convenient Synthesis of Biphenyl-2-carboxylic Acids via the Nucleophilic Aromatic Substitution Reaction of 2-Methoxybenzoates by Aryl Grignard Reagents
Hattori, Tetsutaro,Suzuki, Takatsugu,Hayashizaka, Noriyuki,Koike, Nobuyuki,Miyano, Sotaro
, p. 3034 - 3040 (2007/10/02)
Nucleophilic aromatic substitution (SNAr) of 2-methoxybenzoic esters derived from 2,6-dialkylphenols by aryl Grignard reagents affords 1,1'-biphenyl-2-carboxylates in excellent yields by proper choice of the bulk of the 2,6-dialkyl-substituents. The phenoxyl protecting groups can be easily removed from the resulting biphenyl-2-carboxylates to the free acids by treatment with potassium hydroxide in aqueous ethanol (2,4,6-trimethylphenyl and 2,6-diisopropylphenyl esters) or sodium methoxide in toluene-hexamethylphosphoric triamide (2,6-di-t-butyl-4-methylphenyl esters). The regioselective biphenyl coupling reaction via the SNAr process is utilized for the key-step construction of the biphenyl skeleton in a formal synthesis of cannabinol.
A Practical and Efficient Method for the Construction of the Biphenyl Framework; Nucleophilic Aromatic Substitution on 2-Methoxybenzoates with Aryl Grignard Reagents
Hattori, Tetsutaro,Suzuki, Takatsugu,Miyano, Sotaro
, p. 1375 - 1376 (2007/10/02)
Treatment of 2-methoxybenzoic esters derived from 2,6-dialkylphenols with aryl Grignard reagents afforded 1,1'-biphenyl-2-carboxylates in excellent yields.
