Tetrabutylammonium Fluoride Trihydrate → 2-tert-Butyl-3-bromo-4-iodopyridine

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Reaction Steps

A solution of 14.8 g (36 mmol) of 2-tert-butyl-3-bromo-4-iodo-6-trimethylsilylpyridine and 14.0 g (40 mmol) of tetrabutylammonium fluoride trihydrate in 150 ml of THF is heated under reflux for 5 min. After cooling and removal of the THF in vacuo, the residue is taken up in 200 ml of dichloromethane, the org. phase is washed five times with 100 ml of water each time and dried over sodium sulfate. After removal of the dichloromethane in vacuo, the residue is recrystallised from ethanol. Yield: 9.2 g (27 mmol), 75%. Purity: >95% according to 1H-NMR.

Provenance & Evidence