1,3-Diphenylisobenzofuran synthesis
- Product Name:1,3-Diphenylisobenzofuran
- CAS Number:5471-63-6
- Molecular formula:C20H14O
- Molecular Weight:270.32
4122-56-9
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100-58-3
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5471-63-6
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Yield:5471-63-6 85.3%
Reaction Conditions:
Stage #1: methyl o-formylbenzoate;phenylmagnesium bromide in tetrahydrofuran at -40 - 0; for 1 h;
Stage #2: with trifluoroacetic acid in tetrahydrofuran at 25; for 1.5 h;
Steps:
General Procedure A: Synthesis of Symmetrical Diarylisobenzofuran
General procedure: To a solution of methyl 2-formylbenzoate (50.5 mg, 0.308 mmol) in THF (2.0 mL) was added PhMgBr (1.0 M in THF, 0.72 mL, 0.72 mmol) at -40 °C, and the reaction was warmed to 0 °C. After 1 h, CF3CO2H (181 mg, 1.59 mmol) in THF (1 mL) was added to the mixture, and the reaction was stirred at 25 °C for further 1.5 h. The reaction was stopped by adding sat. aq. NaHCO3. The products were extracted with EtOAc (X3), washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by PTLC (hexane/Et2O = 9/1) to gived iphenylisobenzofuran 3a (70.9 mg, 85.3%). Recrystallization from hexane/EtOAc gave 3a as yellow needles.
References:
Hamura, Toshiyuki;Nakayama, Ryosuke [Chemistry Letters,2013,vol. 42,# 9,p. 1013 - 1015] Location in patent:supporting information
1159-86-0
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5471-63-6
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$18.00/1g