6-bromo-3,4-dihydro-1,3-benzoxazin-2-one

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