Ethyl 4-BroMo-2-fluorobenzoate synthesis

Yield:474709-71-2 90%

Reaction Conditions:

with N,N-dimethyl-4-aminopyridine;N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride in dichloromethane at 20; for 20 h;

Steps:

27.1

Step 1. Preparation of ethyl 4-bromo-2-fluorobenzoate To a stirred solution of 4-bromo-2-fluorobenzoic acid (1.50 g, 6.85 mmol) in DCM (26.0 mL) was added EDCI (1.60 g, 8.35 mmol), DMAP (130 mg, 1.06 mmol), and EtOH (2.00 mL) at room temperature. After being stirred for 20 hours at room temperature, the reaction mixture was washed with water and brine. The organic phase was dried over Na₂SO₄, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO₂ (Hexanes/EtOAc=1/5) to give the desired product (1.52 g, 90%) as a colorless oil. ¹H-NMR (400 MHz, CDCl₃) δ 1.39 (3H, t, J=6.8 Hz), 4.39 (2H, q, J=6.8 Hz), 7.32-7.37 (2H, m), 7.80-7.84 (1H, m).

References:

US2012/53180,2012,A1 Location in patent:Page/Page column 29