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Contrary to literature reports, bromination of 3-hydroxybenzaldehyde can afford both 2-bromo-5-hydroxybenzaldehyde and 2-bromo-3-hydroxybenzaldehyde, but 4-bromo-3-hydroxybenzaldehyde was not detected. 2-Bromo-3-hydroxybenzaldehyde was converted into 2-(benzyloxy)-1-bromo-5-methoxy-7-methylnaphthalene. X-ray crystallographic analysis supports the identity of 2-bromo-3-hydroxybenzaldehyde.
The synthesis of racemic 5-iodo-6,8-dimethoxy-1,3-trans-dimethylisochroman (16) in eleven steps from 2,4-dimethoxybenzaldehyde is outlined. Compound (16) was coupled by means of Suzuki methodology with 4-isopropoxy-5-methoxy-7-methylnaphthaleneboronic acid (19) to yield (20). This was converted into (6), a racemic isochroman analogue of the michellamines.
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