ChemicalBook CAS DataBase List (E)-2-(2-fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(E)-2-(2-fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane synthesis

8synthesis methods

Product Name:(E)-2-(2-fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
CAS Number:633327-38-5
Molecular formula:C14H18BFO2
Molecular Weight:248.1

766-49-4 Synthesis

766-49-4
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(E)-2-(2-fluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

633327-38-5
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Yield:633327-38-5 99%

Reaction Conditions:

with (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride;LiNP^tBu₃ in benzene at 20; for 13 h;Glovebox;Inert atmosphere;stereoselective reaction;

Steps:

III. Procedure for the Cu(I)-Catalyzed Alkyne Hydroboration Reaction 1. Cu (I) catalyzed hydroboration of terminal alkyne (Table 2)

General procedure: In an N₂ charged glove box with oxygen and water levels ≤0.1 ppm, to an oven-dried screwed vial were added SIPrCuCl (c8) (4.9 mg, 5 mol%, 0.01 mmol), tri(t-Butyl)phosphoranimide (1b) (2.2 mg, 5 mol%, 0.01 mmol), Pinacolborane (1c) (28 mg, 0.22 mmol, 1.1 eq.), terminal alkyne (1) (0.2 mmol, 1 eq.) and benzene (2 mL, 0.1 M). The formed reaction mixture was kept stirring for 13-15 hours in glove box. Then the dark brown reaction mixture was taken out from glove box the solvent was removed by rotary evaporator. The solvent mixture (Hexane:Ethyl acetate) was added into the reaction residue as eluent then kept stirring for about 30 mins under room temperature until the precipitate was formed. The mixture was further filtered through a short pad of silica gel to get colorless filtrate. Organic solvents were removed under reduced pressure and desired product was obtained after dryness under vacuum without further purification.

References:

Bai, Tao;Yang, Yanhui;Han, Chao [Tetrahedron Letters,2017,vol. 58,# 15,p. 1523 - 1527] Location in patent:supporting information

704-97-2 Synthesis