Methyl 3-Methoxy-5-(trifluoroMethyl)benzoate synthesis

Yield:1003843-90-0 95%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 40; for 20 h;

Steps:

71.15

15). Synthesis of 1-bromomethyl-3-methoxy-5-trifluoromethyl-benzene; A solution of 3-hydroxy-5-(trifluoromethyl)benzoic acid (1.03 g, 5 mmol) and K₂CO₃ (2.07 g, 15 mmol) in DMF (50 mL) is added methyl iodide (1.09 ml_, 17.5 mmol) allowed to warm to 40 ⁰C and stir for 20 hours. The mixture is cooled to room temperature, then added water. The mixture is extracted with ethyl acetate. The combined organic layer is washed with brine, dried over Na₂SO₄, filtrated, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: hexane / EtOAc) to give 3- methoxy-5-trifluoromethyl-benzoic acid methyl ester (1.11 g, 95%); ESI-MS m/z: 235 [M+1] Retention time 2.06 min (condition A).

References:

WO2008/9435,2008,A1 Location in patent:Page/Page column 161