Dichloromethane → 4-(4-Bromo-3-fluorobenzyl)morpholine

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A mixture of morpholine (0.215 ml, 2.46 mmol) and 4-bromo-3-fluorobenzaldehyde, available from Alfa Aesar, (500 mg, 2.46 mmol) was prepared in chloroform (8 ml) at room temperature and heated to 58-60° C. in a sealed tube for 1 h. The mixture was then cooled to room temperature and sodium triacetoxyborohydride (783 mg, 3.69 mmol) was added and the mixture heated again to 58-60° C. in a sealed tube for 12 h. The mixture was then allowed to cool to room temperature, diluted with water (4 ml), shaken vigorously and the mixture filtered through a phase separator and the filtrate concentrated in vacuo. The mixture was then purified by SCX-2 chromatography (Eluent: dichloromethane (2×10 ml), 10% methanol/dichloromethane (2×10 ml), methanol (2×10 ml), 7M NH3 in methanol/dichloromethane (2×10 ml) to afford 4-(4-bromo-3-fluorobenzyl)morpholine as a colourless oil (447 mg, 1.63 mmol, 66%).

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