ChemicalBook CAS DataBase List 1-CHLORO-3-(1-PHENYL-VINYL)-BENZENE

1-CHLORO-3-(1-PHENYL-VINYL)-BENZENE synthesis

10synthesis methods

Product Name:1-CHLORO-3-(1-PHENYL-VINYL)-BENZENE
CAS Number:29265-81-4
Molecular formula:C14H11Cl
Molecular Weight:214.69

1016-78-0
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$7.00/5g

1779-49-3
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$5.00/10g

29265-81-4
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$65.00/50mg

Yield:29265-81-4 82%

Reaction Conditions:

Stage #1: Methyltriphenylphosphonium bromidewith n-butyllithium in tetrahydrofuran at 0 - 20; for 0.5 h;Inert atmosphere;Wittig Olefination;
Stage #2: 3-chlorobenzophenone in tetrahydrofuran at 20;Inert atmosphere;Cooling;Wittig Olefination;

Steps:

Typical procedure for the synthesis of 5a-i and 5k-5p

General procedure: Ph₃PCH₃Br (1.20 equiv) was added to a flame-dried round-bottom flask, evacuated, backfilled with N₂ three times, and suspended in THF (0.25 M) at 0°C. To this vigorously stirring heterogeneous solution was added ⁿBuLi (1.20 equiv) dropwise, and the reaction was allowed to stirred at room temperature for 30 min until a bright yellow heterogeneous mixture was achieved. Then commercially available 1,1-diarylmethanone (1.00 equiv) was added slowly. Upon complete addition, the cooling bath was removed and the reaction was allowed to stir overnight. Then, the solution was washed by brine and extracted with EtOAc (3×10 mL). The combined organic layers were dried over MgSO₄, and concentrated under vacuum. The residue was purified by silica gel flash chromatography (PE:EA = 100:1) to afford the corresponding 1,1-diarylethene 5 and NMR spectra was compared to known literatures values.

References:

Zhang, Ge;Bai, Rui-Xue;Li, Chu-Han;Feng, Chen-Guo;Lin, Guo-Qiang [Tetrahedron,2019,vol. 75,# 12,p. 1658 - 1662] Location in patent:supporting information

98-81-7 Synthesis