Synthesis of vinylmagnesium bromide

Preparation of vinylmagnesium bromide

Preparation of vinylmagnesium bromide

Preparation of vinylmagnesium bromide

1.5 mol or 36 g) of well-dried magnesium turnings are covered with 100 ml of dry tetrahydrofuran 4 ml of 1 ,2-dibromoethane is added with stirring. After the exothermic reaction has ceased, the THF is cooled to 35° C. A mixture of 1.1 mol (118 g) of vinyl bromide and 250 ml of  THF is added dropwise over a period of 2.5 h, while keeping the temperature of the dark-grey solution between 35 and 40° C. At lower temperatures salt will crystallize out, causing the conversion to proceed less smoothly. During storage (at room temperature) great quantities of salt precipitate. Before using part of the solution, the flask should be warmed (with swirling) until the salt has dissolved. After the addition, stirring and heating at 40° C are continued for another hour. The warm solution is transferred (under a blanket of inert gas) into a calibrated flask, which previously has been filled with inert gas. The excess magnesium is rinsed twice with 30 ml portions of dry tetrahydrofuran, the rinsings being added to the solution in the flask. A small amount of dry tetrahydrofuran is added to bring the volume to 500 ml at 35-40° C, after which the flask is shaken for homogenization. The yield is at least 90 %, and thus the solution contains about 1.0 mol of vinylmagnesium bromide.

Preparative Polar Organometallic Chemistry; Vol 1; by L. Brandsma, H. D. Verkruijsse; Springer-Verlag Berlin Heidelberg; 47-48; 1987

IUPAC Name

magnesium;ethene;bromide

InChI

InChI=1S/C2H3.BrH.Mg/c1-2;;/h1H,2H2;1H;/q-1;;+2/p-1

InChI Key

RMGJCSHZTFKPNO-UHFFFAOYSA-M

Canonical SMILES

C=[CH-].[Mg+2].[Br-]

Depositor-Supplied Synonyms

Vinylmagnesium bromide, Vinylmagnesium bromide solution, Magnesium, bromoethenyl-, bromo(ethenyl)magnesium, SCHEMBL1224, 225584_ALDRICH, 257257_ALDRICH, AC1Q23T4, Jsp003743, 95008_FLUKA, MolPort-003-928-123, EINECS 217-375-3, AKOS015901812, OR037805, FT-0689130, I14-13891, Vinylmagnesium bromide, 1.0M solution in Tetrahydrofuran

Removed Synonyms

Bromovinylmagnesium, Bromovinyl magnesium, Magnesium,bromoethenyl-, CID74584, 1826-67-1

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