ChemicalBook CAS DataBase List 9-Methylene-9H-fluorene

9-Methylene-9H-fluorene synthesis

10synthesis methods

Product Name:9-Methylene-9H-fluorene
CAS Number:4425-82-5
Molecular formula:C14H10
Molecular Weight:178.23

A suspension of methyl triphenylphosphonium bromide (31.22 g; 87.3 mmol) in 500 mL of ether was added at -30°C. 10M n-butyllithium in hexane (8.73 mL; 87.3 mmol) was added to the mixture, and the mixture was stirred at room temperature for 1-2 hours. To the above mixture, 15 g (83.2 mmol) of 9-fluorenone in 50 mL of tetrahydrofuran was added, and the mixture was refluxed for 1 hour. After cooling the above mixture to 0°C, 9-Methylene-9H-fluorene was obtained after purification.
9-methylidenefluorene

24324-17-2 Synthesis

24324-17-2
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4425-82-5
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Yield:4425-82-5 100%

Reaction Conditions:

with 1H-imidazole;PS-triphenylphosphine;iodine in dichloromethane;not specified; for 0.5 h;Heating / reflux;

Steps:

Compound 204a:; 204aTo a dichloromethane solution (35 imL) of triphenylphosphine (polymer-supported, 3 mmol/g, 1.87 g, 5.61 mmol) was added I₂ (1.42 g, 5.61 mmol). The mixture was stirred for 15 minutes. Imidazole (410 mg, 6.38 mmol) was introduced and stirred gently at room temperature for another 15 minutes. 9- Fluorenyl methanol (500 mg, 2.55 mmole) was then introduced into the reaction mixture and refluxed for 30 minutes. It was filtered through a pad of celite. The filtrate was diluted with dichloromethane (30 mL), washed with saturated Na₂S₂O₃ (30 mL), water (30 mL) and brine (30 nriL), dried with Na₂SO₄ and concentrated to give the title compound in 100% yield. ¹H NMR (DMSO- d₆): δ 7.88 (2H, d, J=7.3Hz), 7.83 (2H, d, J=7.6Hz), 7.41 (2H, td, J=7.6, 1.1 Hz), 7.33 (2H, td, J=7.6, 1.3Hz), 6.27 (2H, s). LCMS (APCI): 179.0 (M+H⁺).

References:

WO2006/40646,2006,A1 Location in patent:Page/Page column 130