Improved Regioselectivity of Lithiation of Methoxybenzaldehydes

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Abstract
Protection of the aldehyde moiety as a N,N'-diisopropylimidazolidine allows improved preferential lithiation ortho to the methoxy group of 4- methoxybenzaldehyde or in the 4-position of 3-methoxybenzaldehyde. Reaction with a suitable electrophile, such as dimethyldisulphide, gives good yields of 3-substituted-4-methoxybenzaldehydes or moderate yields of 4-substituted-3-methoxybenzaldehydes as appropriate.