Hydrochloric Acid → 2-(Methoxymethoxy)-3-methylphenylboronic acid

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Reaction Conditions

Reaction Steps

To a solution of 1-(methoxymethoxy)-2-methylbenzene in diethyl ether (0.3M) cooled at −60° C. tBuLi in pentane (1.7M, 1.4 eq) was added dropwise and the mixture was stirred for 1 h while warming gradually to 0° C. then for further 2 h at 0° C. The mixture was cooled to −78° C. and a solution of B(OMe)3 in THF (3 eq, 3.0M) was added dropwise and the mixture was allowed to reach RT and stirred overnight. The mixture was cooled to 0° C. and 1N HCl was added, then the reaction mixture was stirred for 2 h. All volatiles were removed under reduced pressure and the residue was extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over Na2SO4, filtered and evaporated in vacuo to give a yellow solid which was triturated with PE to give a white solid which was used in the next step without further purification.

Provenance & Evidence