2,5-bis(morpholin-4-ylmethyl)benzene-1,4-diol

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

Procedure: To a solution of 2,5-bis-(morpholinomethyl)-hydroquinone (100 mg, 0.324 mmol) in THF was added sodium hydride (26 mg of 60% dispersion in mineral oil) followed by 2-nitro-4-(trifluoromethylsulfonyl)chlorobenzene (188 mg, 0.648 mmol). The mixture was stirred at room temperature for overnight. The reaction was extracted with ethyl acetate, the organic layer was washed with water and brine, dried, concentrated and purified to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.81 (d, J=2.2 Hz, 2H), 8.23 (m, 2H), 7.60 (s, 2H), 7.27 (m, 2H), 3.4 (m, 4H, 2×CH2), 3.06 (m, 8H, 4×CH2), 2.18 (m, 8H, 4×CH2). MS 815 [M++1]. The reaction was extracted with ethyl acetate the organic layer was washed with water and brine dried concentrated purified