Boronic acid, B-(6-phenyl-4-dibenzofuranyl)- synthesis
- Product Name:Boronic acid, B-(6-phenyl-4-dibenzofuranyl)-
- CAS Number:1010068-85-5
- Molecular formula:C18H13BO3
- Molecular Weight:288.11
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Yield:1010068-85-5 85%
Reaction Conditions:
Stage #1: 4-phenyldibenzo[b,d]furanwith n-butyllithium in tetrahydrofuran at -78 - 20; for 5 h;
Stage #2: Trimethyl borate in tetrahydrofuran at -78 - 20;
Steps:
[0118] Synthesis of (6-phenyldibenzo[b,d]furan-4yl)boronic acid: n-Butyllithium (13.51 mL, 33.8 mmol) was added dropwise to 4-phenyldibenzo[b,d]furan (3.3 g, 13.51 mmol) in 80 mL dry THF at -78 °C. This reaction mixture was allowed to stir at room temperature for 5 hours and then cooled to -78 °C again. Trimethyl borate (4.52 mL, 40.5 mmol) was added slowly to the reaction. The reaction mixture was allowed to warm up to room temperature gradually over night with stirring. The mixture was poured into 50 mL of NH4OH solution with ice. The aqueous mixture was extracted with 3x80 mL ethyl acetate and dried over sodium sulfate, and the organic layer was evaporated to get yield 3.3 g (85%) product, which was used without purification and was confirmed by NMR.
References:
EP2594573,2013,A1 Location in patent:Paragraph 0118
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