methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate synthesis

13synthesis methods

Product Name:methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate
CAS Number:890839-11-9
Molecular formula:C16H23BO4
Molecular Weight:290.16

2-(4-BroMo-phenyl)-propionic acid Methyl ester

83636-46-8
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73183-34-3
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methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

890839-11-9
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Yield:890839-11-9 92%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane; for 6 h;Inert atmosphere;Reflux;

Steps:

4.28. Methyl 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]propionate (44)

A mixture of Methyl 2-(4-bromophenyl)propionate (38) (5g, 20.56 mmol), potassium acetate (4.04 g, 41.11 mmol), Bis(pinacolato)diboron (10.45 g, 41.13 mmol) and [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.84 g, 1.03 mmol) in 1,4-dioxane (100 mL) was refluxed for 6 h under nitrogen atmosphere. The reaction mixture was cooled to 60 °C and concentrated under reduced pressure. Water (50 mL) and ethyl acetate (50 mL) were charged, stirred for 30 min and filtered through celite. Organic layer was separated, dried over sodium sulfate and concentrated. The residue was purified using column chromatography (silica gel, 3-5 % ethyl acetate in hexane) to afford Methyl 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaboralan-2-yl)phenyl]propionate (44) (5.5 g, 92 %) as a colourless syrup: ¹H NMR (400 MHz, CDCl3) δ 7.78 (d, J = 7.6 Hz, 2H), 7.32 (d, J = 8.4 Hz, 2H), 3.73 (q, J = 6.8 Hz, 1H), 3.63 (s, 3H), 1.50 (d, J = 7.2 Hz, 3H), 1.32 (s, 12H); ¹³C NMR (100 MHz, CDCl3) δ 174.72, 143.73, 135.18, 134.97, 126.89, 124.98, 83.76, 52.02, 45.61, 24.85, 18.50; IR (KBr) ν_max 2980.90, 1740.69 cm_-1; MS: m/z 291.1 (M + H)⁺.

References:

Bhatthula, Bharath kumar goud;Kanchani, Janardhan reddy;Arava, Veera reddy;Subha [Tetrahedron,2019,vol. 75,# 7,p. 874 - 887]