2-(aminomethyl)-4-bromophenol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(aminomethyl)-4-bromophenol (I) (1.16 g, 5.7 mmol), triethylamthylamine (III) and carbonyldiimidazole (II) (1.86 g, 11.5 mmol) in anhydrous THF (100 ml) is refluxed for 4 hours. The solvent is evaporated and the residue dissolved in dichloromethane (DCM) (100 ml). The organic solution is washed with 1N HCl (20 ml×3) and then with brine (50 ml). The solvent is then evaporated and the resulting residue is purified by chromatography to give 6-bromo-3,4-dihydrobenzo[e][1,3]oxazin-2-one as a white powder. The solvent is evaporated the residue dissolved in dichloromethane (DCM) (100 ml) The organic solution is washed with 1N HCl (20 ml×3) The solvent is then evaporated the resulting residue is purified by chromatography

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. capped round-bottom flask The reaction mixture is refluxed for 3 hours 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) 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 washed with water The product is further dried in vacuum oven overnight