Triethylamine → HCID 66616643, compound

Participants

Reaction Steps

To a solution of methyl 4-(bromomethyl)-3-methoxybenzoate (0.518 g, 2 mmol, Trans World Chemicals) in THF (10 mL) at room temperature was added (4-fluorophenyl)methanamine (1.00 g, 8.00 mmol, Aldrich) and triethylamine (0.56 mL, 4 mmol). The reaction mixture was stirred at rt for 1 h and quenched by the addition of 5 mL of saturated aq. NaHCO3 solution. The resulting mixture was extracted with DCM (3×50 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography (ISCO system, eluting with CH2Cl2/EtOAc) to give the desired compound (0.35 g, 57%) as a white solid. 1H NMR (CD3OD) δ 7.64 (d, 1H, J=6.0 Hz), 7.60 (s, 1H), 7.40 (d, 2H, J=7.7 Hz), 7.36 (d, 1H, J=6.0 Hz), 7.08 (t, 211, J=7.7 Hz), 3.97 (s, 3H), 3.96 (s, 3H), 3.82 (s, 2H), 3.76 (s, 2H). MS (ESI): 304.1 (M+H)+.

Provenance & Evidence