ChemicalBook CAS DataBase List 2-Methyl-1,1'-binaphthalene

2-Methyl-1,1'-binaphthalene synthesis

12synthesis methods

Product Name:2-Methyl-1,1'-binaphthalene
CAS Number:118018-45-4
Molecular formula:C21H16
Molecular Weight:268.35

90-14-2
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103989-84-0
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118018-45-4
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Yield:118018-45-4 100%

Reaction Conditions:

with tris-(dibenzylideneacetone)dipalladium⁽⁰⁾;potassium carbonate in tetrahydrofuran at 20; for 2 h;Inert atmosphere;Suzuki coupling;

Steps:

6. General procedure for coupling reactions of aryl halides with organoboronic acids

General procedure: A typical procedure is given for the reaction represented by Entry 8 in Table 1. Ligand 2e (6 mg, 0.01 mmol), Pd₂(dba)₃ (5 mg, 0.005 mmol), 2-methylnaphthyl-1-boronic acid (223 mg, 1.2 mmol), Cs₂CO₃ (975 mg, 3 mmol) were introduced to a flask under N₂ gas. 1-bromo-2-methylnaphthalene (221 mg, 1 mmol) was added into the flask, followed by addition of THF (5 ml) by a syringe. The mixture was stirred under reflux for 24 h, under ambient pressure of N₂. The solvent was then removed under reduced pressure. The resultant residual mixture was diluted with H₂O (10 ml) and Et₂O (10 ml), followed by extraction twice with Et₂O. The organic extract was collected and stripped of solvent under vacuum. The product was isolated by column chromatography on silica eluting with hexane/ethyl acetate to give 276 mg (98%) of 2,2'-dimethyl-1-1'-binaphthalene as a solid, which was verified by GC/MS.

References:

Teo, Shihui;Weng, Zhiqiang;Hor, T.S. Andy [Journal of Organometallic Chemistry,2011,vol. 696,# 17,p. 2928 - 2934] Location in patent:experimental part

2586-62-1 Synthesis