Methanol → HCID 53747526, compound

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-5-methoxy-4-propylphenyl triflate (3.00 g, 9.5 mmol), triethylamine (2.91 mL, 20.9 mmol) and methanol (7.0 mL, 173 mmol) were dissolved in DMF (30 mL) and the solution was flushed with CO. 1,3-Bis(diphenylphosphino)propane (151 mg, 0.37 mmol) and palladiumacetate (84 mg, 0.37 mmol) were added and the reaction was stirred at 70° C. and atmospheric pressure for 4.5 h. Evaporation of the solvent and co-evaporation with xylene gave a residue which was extracted between Et2O and 2M NaOH and the organic phase was washed brine, dryed over MgSO4 and evaporated to give 2.3 g of crude product. Purification by flash chromatography (SiO2, CH2Cl2 -hexane 1:2) gave methyl 2-fluoro-5-methoxy-4-propylbenzoate (1.46 g) as an oil. 1H NMR (DMSO-d6): δ7.28 (d, J=6.0 Hz, 1H), 7.12 (d, J=11.4 Hz, 1H), 3.83 (s, 3H), 3.80 (s, 3H), 2.54 (t, J=7.6 Hz, 2H), 1.53 (m, J=7.6 Hz, 2H), 0.87 (t, J=7.4 Hz, 3H). 13C NMR (DMSO-d6): δ164.01 (d, J=4 Hz), 155.21 (d, J=251 Hz), 152.95, 138.30 (d, J=8 Hz), 117.93 (d, J=24 Hz), 115.26 (d, J=11 Hz), 111.75, 55.88, 52.20, 31.32, 21.83, 13.66. MS (EI, 70 eV): m/z (rel. int) 226 (M+, 100).

Provenance & Evidence