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dark brown solution

Ethylmagnesium bromide is a Grignard reagent widely used in organic chemical synthesis. It can be employed in the following chemical reactions:
(1) The cleavage effect on pentafluorophenylphosphine bonds and sulphur bonds: Reactions between tri(pentafluorophenyl)phosphine and bis(pentafluorophenyl)sulphide with ethylmagnesium bromide yield products indicating the pentafluorophenyl group detaches from both phosphorus and sulphur^[1].
(2) Reaction with unsaturated organotin compounds to form saturated compounds: Its reaction with tri-n-butylstannylacetylene in diethyl ether removes ethane, ethylene, acetylene, and ethylacetylene, yielding ethyl tri-n-butylstannyl and bis-1,2-tri-n-butylstannyl ethane^[2].
(3) Facilitating selective transformation of cyclopropyl groups: In the case of the tetrahydrofuran-protected racemic diethyl malonate 1, selective conversion of the cyclopropyl group is achieved via a reductive cyclopropanation reaction using ethylmagnesium bromide in the presence of tetrahydrofuran. This ultimately enables the isolation of the ethoxycarbonyl group from diethyl malonate^[3].

Ethylmagnesium bromide is commercially available, usually as a solution in diethyl ether or tetrahydrofuran. It may be prepared in the normal manner of Grignard reagents — by reacting bromoethane with magnesium in diethyl ether:
EtBr + Mg → EtMgBr

Ethylmagnesium bromide reacts with water to produce ethane.
CH3CH2MgBr+H2O→CH3-CH3+Mg(OH)Br

reaction type: Grignard Reaction

[1] STEPHEN A. SICREE Christ T. Cleavage of pentafluorophenyl-phosphorus and -sulfur bonds by ethylmagnesium bromide[J]. Journal of Fluorine Chemistry, 1992, 59 2: Pages 269-273. https://doi.org/10.1016/S0022-1139(00)82419-7.
[2] A. N. NESMEYANOV I. S S A E BORISOV. ChemInform Abstract: REACTIONS OF ETHYLMAGNESIUM BROMIDE WITH SOME UNSATURATED ORGANOTIN COMPOUNDS[J]. ChemInform, 1976, 7 4. https://doi.org/10.1002/chin.197604258.
[3] ANDREI V. BEKISH Oleg G K. Differentiation between the ethoxycarbonyl groups in diethyl malate via their titanium-catalyzed reductive cyclopropanation with ethylmagnesium bromide and subsequent site-selective three-carbon ring cleavage[J]. Tetrahedron Letters, 2005, 46 41: Pages 6975-6978. https://doi.org/10.1016/j.tetlet.2005.08.076.