O-Methoxyphenylmagnesium bromide

A. 4-Dimethylamino-2 -methoxybmzhydrol. An ethereal solution of o-methoxyphenylmagnesium bromide is prepared in the usual manner2 with 250 ml. of anhydrous ether, 14.5 g. (0.60 g. atom) of magnesium, and 100 g. (0.53 mole) of o-bromoanisole (Note 1). A solution of 60 g. (0.40 mole) of />-dimethylamino-benzaldehyde (Note 2) in 200 ml. of anhydrous benzene is added dropwise to the Grignard reagent (Note 3). After the addition is completed, the reaction mixture is stirred for 10 hours at room... 

N, 4,4-trimethyl-2-oxoazolinium iodide. The system is flushed with nitrogen, and 150 ml. of tetrahydrofurane distilled from lithium aluminum hydride is added and the stirred suspension is cooled in an ice bath. Meanwhile, to a cooled solution of freshly prepared o-methoxyphenylmagnesium bromide (0.414 mole) from o-bromoanisole (77.5 g.,... 

The enantiomeric di-O-methyl ethers were prepared as follows. Addition of p-methoxyphenylmagnesium bromide onto 336 led to a... 

The yellow diamagnetic o-anisole derivative is also prepared from CrCh or CrBr2(THF)2 and 2-methoxyphenylmagnesium bromide in THF °. A more convenient route to phenyl derivatives involves substitution of Cr2(OAc)4 (see 9.2.12). 

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