Hydrogen Bromide → 4-[2-(4-Bromomethyl-naphthalen-1-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole

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Reaction Steps

0.494 g of 5-Methyl-4-[2-(naphthalen-1-yloxy)-ethyl]-2-phenyl-oxazole (1.50 mmol) was dissolved under argon atmosphere in 6 ml of CH2Cl2 and cooled down to 0°. 0.455 ml of 62% aq. HBr was added, followed by 58 mg of trioxane (0.644 mmol, 1.29 eq.). After 2 h, additional 0.455 ml of 62% aq. HBr was added and stirring continued for totally 5 h under strict temperature control. The reaction mixture was then diluted with CH2Cl2, washed with sat. NaHCO3-sol., the aqueous layer extracted once more with CH2Cl2, the combined organic phases dried over sodium sulfate and evaporated to dryness. This left 0.70 g of the crude title compound which was used as such for the next step. The product is quite unstable and can not be purified by column chromatography on SiO2; it also decomposes readily on TLC-plates.

Provenance & Evidence