Methanol → HCID 10848200, compound

Participants

Reaction Steps

2,4-Dichloro-5-methoxy-3-methylphenyl triflate (7.60 g, 22.4 mmol) was dissolved in dioxan (75 mL), 1,3-bis (diphenylphosphino)propane (371 mg, 0.90 mmol) and palladium acetate (202 mg, 0.90 mmol) were added. After flushing with CO, Et3N (6.90 mL, 49.4 mmol) and MeOH (23 mL) were added. Reaction with CO at 70° C. and at atmospheric pressure for 25° C., filtration and evaporation, of the solvent partition of the residue between Et2O (350 mL) and 3M NH3 (150 mL), extraction of the aqueous layer with Et2O (2×150 mL) followed by washing the combined organic phase with brine (150 mL), drying (MgSO4), evaporation of the solvent gave a crude product. Filtration through SiO2 using EtOAc as the eluent gave 5.2 g of a product which was purified by flash column chromatograhy (SiO2, EtOAc-Hexane 1:3) to yield 4.18 g of the title compound. Mp: 74° C.; 1H NMR(DMSO-d6): δ 7.33 (s, 1H), 3.88 (s, 3H), 3.86 (s, 3H), 2.45 (s, 3H); 13C NMR (DMSO-d6) : δ 165.69, 153.26, 136.09, 130.46, 125.22, 122.95, 110.78, 56.64, 52.72, 17.86; MS (EI, 70 eV): m/z (rel.int.) 250/248 (M+, 53/80), 219/217 (66/100), 191/189 (8/12).

Provenance & Evidence