2H-1,4-Benzoxazine, 6-bromo-3,4-dihydro-4-(phenylmethyl)- synthesis

Yield:1148008-74-5 95%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20;

Steps:

48.b

b) 6-bromo-4-(phenylmethyl)-3,4-dihydro-2H-l,4-benzoxazine; A suspension of 6-bromo-3,4-dihydro-2H-l,4-benzoxazine (0.150 g, 0.70 mmol), potassium carbonate (0.242 g, 1.75 mmol), and benzyl bromide (0.179 g, 1.049 mmol) in dry DMF (1.5 mL) was stirred overnight at room temperature. The reaction was diluted with water and EtOAc and transferred to a separatory funnel. The layers were separated and the water was extracted twice with EtOAc. The combined EtOAc layers were washed with water and saturated NaCl, dried over Na₂SO₄, filtered and concentrated to give the title compound (0.203 g, 95%) as a slightly pink crystalline solid. MS(ES)⁺ m/e 305 [M+η].

References:

WO2009/55418,2009,A1 Location in patent:Page/Page column 70