Ethylmagnesium bromide 2-

A 20% excess of ethylmagnesium bromide was prepared from magnesium (6.5 g) in ether (80 ml) by adding ethyl bromide (30 g) in ether (30 ml). Indole (25.8 g) in benzene (50 ml) was then added slowly with stirring and stirring was continued for 20 min after addition was complete. A solution of allyl bromide (29.2 g) in benzene (20 ml) was then added slowly. The mixture was stirred overnight and then diluted with ether and the product isolated and purified by distillation (22.7 g, 70% yield). 

Under the action of strong organometallic bases, thiazole undergoes hydrogen-metal interconversion. Ethylmagnesium bromide reacts at 0°C with thiazole in ether to form an insoluble adduct that upon heating evolves ethane almost quantitatively and affords an etheral solution of thiazol-2-ylmagnesium bromide (155) (12). Proof of the structure of this... 

Alkylthiazoles react with ethylmagnesium bromide to give thiazolyl-magnesiurn compounds, as demonstrated for 4- and 5-methyithiazoles, 4-ethylthiazole. and 4,5-dimethylthiazole. The resulting addition compounds do not decompose at high temperature and pressure to yield alkylthiazoles as do the addition compounds obtained with pyridine. 

Problem 14 7 at the end of the preceding section intro duced this idea with the sug gestion that ethylmagnesium bromide be represented as ethyl anion... 

The reaction of 4-bromo- or 4-iodo-isoxazoles with ethylmagnesium bromide gave the... 

Tetraethyltin has been prepared from tin-sodium alloy and ethyl iodide, from tin-sodium-zinc alloy and ethyl bromide, and from tin tetrachloride and ethylmagnesium bromide. The method described is essentially that of Pfeiffer and Schnur-mann. ... 

In addition, there is a cleavage reaction whereby a perfluoroorgamc group is cleaved from a metal by a base, for example, phenyllithium [4], ethylmagnesium bromide [5], or a fluoride ion [6] (equations 3-5)... 

Another similar example is shown by the reaction between ris(pentafluo-rophenyI)tin bromide and ethylmagnesium bromide (equation 8)... 

This section will focus primarily on a comparison of these ring systems with their heavier chalcogen analogues. The first selenium derivative benzo-l,2,5-selenadiazole was prepared more than 115 years ago by the condensation reaction of selenium dioxide with 1,2-diaminobenzene (Eq. 11.12) and other benzo derivatives may be prepared in a similar manner. The parent 1,2,5-selenadiazole has also been reported. This reagent has been employed to make the tellurium analogue via treatment with ethylmagnesium bromide followed by the addition of tellurium tetrachloride (Eq. 11.13). ... 

Methyl-2-phenyl-5-oxazolone (22) reacts with excess phenyl-magnesiuin bromide to give 2-benzainido-1,1-diphenyl-1-propanoP (23). With excess ethylmagnesium bromide, 22 forms a dimer, N,N -... 

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