ChemicalBook CAS DataBase List methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

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

74-88-4

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

890839-11-9

b) General procedure for the synthesis of methyl 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate: under argon protection, a THF solution of methyl 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (1.04 g, 3.78 mmol) ( 3.5 mL, 1.5 M) was added dropwise to THF (6 mL), keeping the reaction temperature at -78 °C. After the dropwise addition, the reaction mixture was slowly warmed up to 0 °C, followed by the addition of iodomethane (3.22 g, 22.6 mmol). The reaction mixture was stirred at room temperature for 1 h. The pH was then adjusted to ~2 by addition of 2 M HCl solution to terminate the reaction. The reaction mixture was extracted with ethyl acetate, the organic phase was concentrated and finally purified by combiflash column chromatography to give a white solid product (0.77 g, 70% yield). The product was characterized by 1H-NMR (CDCl3): δ 1.354 (12H, s), 1.517 (3H, d, J = 7.2 Hz), 3.667 (3H, s), 3.750 (1H, m), 7.323 (2H, d, J = 7.2 Hz), 7.796 (2H, d, J = 7.2 Hz).

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

83636-46-8
29 suppliers
inquiry

73183-34-3
589 suppliers
$6.00/5g

890839-11-9
23 suppliers
inquiry

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]

74-88-4
356 suppliers
$15.00/10g

890839-11-9
23 suppliers
inquiry

References

39718-97-3 Synthesis