9-Borabicyclo(3.3.1)nonane → 4-Fluoro-2,3-dimethoxybenzene butanal

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Reaction Steps

The product from Example 54 (7.2 g) was treated with 9-BBN (85 ml, 0.5M in THF) at room temperature with stirring for 2 hours. The stirring was stopped and the reaction mixture cooled to 0° then potassium triisopropoxyborohydride (43 ml, 1.0M in THF) was added. Carbon monoxide was bubbled through the reaction mixture for 3 hours, then pH 7 buffer (60 ml) and 30% H2O2 (16 ml) was added with stirring and the reaction was allowed to stir overnight. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was separated, dried and evaporated to afford the desired product as an oil.

Provenance & Evidence