Acetic Acid → 4-(3-Bromo-4-fluorobenzyl)morpholine

Participants

Reaction Steps

Morpholine (0.96 mL) and acetic acid (0.57 mL) are added to a solution of 3-bromo-4-fluorobenzaldehyde (2.03 g) in dichloroethane (40 mL). Sodium triacetoxyborohydride (3.18 g) is added in portions over an hour, and the reaction is stirred at room temperature for 18 hours. The reaction is quenched with a 1 N solution of NaOH (10 mL) and diluted with CH2Cl2 (100 mL). The organic layer is washed with 1 N NaOH (3×35 mL). The aqueous layers are back-extracted with CH2Cl2 (20 mL). The combined organic layers are extracted with 0.1 N HCl (6×25 mL). The combined aqueous layers are basified (pH=12) with 2 N NaOH, and the product is extracted with CH2Cl2 (6×25 mL). The combined organic layers are washed with brine (20 mL) and dried (MgSO4). The solution is concentrated in vacuo to afford 2.23 g (82%) of the title compound as a clear, colorless oil.

Provenance & Evidence