ChemicalBook CAS DataBase List (E)-ethyl 3-(3-bromophenyl)acrylate

(E)-ethyl 3-(3-bromophenyl)acrylate synthesis

12synthesis methods

Product Name:(E)-ethyl 3-(3-bromophenyl)acrylate
CAS Number:59114-88-4
Molecular formula:C11H11BrO2
Molecular Weight:255.11

3132-99-8 Synthesis

3132-99-8
482 suppliers
$5.00/10g

65946-56-7 Synthesis

Trimethylsilylketene Ethyl Trimethylsilyl Acetal (mixture of isomers)

65946-56-7
25 suppliers
$130.00/500mg

59114-88-4
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Yield: 76%

Reaction Conditions:

with 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene in acetonitrile at 0 - 20;stereoselective reaction;Peterson Olefination;

Steps:

General procedure for N-heterocyclic carbene-catalysed Peterson olefination reaction
General procedure: NHC 4 (6.0 mg, 0.015 mmol) was added to a solution of aldehyde 2 (0.3 mmol) and silyl ketene acetal (1a or 1b, 0.45 mmol) in anhydrous CH3CN (1.0 mL) at 0 C. The reaction mixture was then stirred at room temperature until full consume of the starting aldehyde indicated by TLC. The ratio of E/Z was determined by 1HNMR analysis of the crude products and the configurations were assigned by 1H NMR comparison with literature.15b,15c The crude product was purified by flash column chromatography on silica gel (PE-EtOAc, 50:1) to give the desired product 3 or 4 as a mixture of inseparable Z and E-isomers.

References:

Wang, Ying;Du, Guang-Fen;Gu, Cheng-Zhi;Xing, Fen;Dai, Bin;He, Lin [Tetrahedron,2016,vol. 72,# 4,p. 472 - 478]