Iodine → 2-(Aminomethyl)-4-bromophenol

Participants

Reaction Conditions

Reaction Steps

5-bromo-2-hydroxybenzamide (2.16 g, 10 mol) and NaBH4 (1.52 g, 40 mol) are dissolved in dry THF (150 ml) in a two-neck septum capped round-bottom flask. Iodine (5.06 g, 20 mol)) in dry THF is added under nitrogen atmosphere at 0° C. over 2.5 hours. The reaction mixture is refluxed for 3 hours and then cooled to 0° C. The excess hydride is destroyed by careful addition of 1N HCl. After removing most organic solvent by vacuum, the acidic aqueous solution is diluted in 1N HCl (150 ml) and washed three times with ether (30 ml each time). The pH of the aqueous solution is adjusted to pH=6-7 by careful addition of sodium bicarbonate solid. The product is collected by filtration and then washed with water. The product is further dried in vacuum oven overnight giving 2-(aminomethyl)-4-bromophenol which is used directly in the next step without further purification.

Provenance & Evidence