Methanol → Methyl 2-chloro-4-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

To 4-bromo-3-chlorotoluene (4.97 g, 24.2 mmol) in DMF (25 mL) is added Pd(OAc)2 (0.54 g, 2.42 mmol), 1,3-bis(diphenylphosphino)propane (0.998 g, 2.42 mmol), triethylamine (12.5 mL) and methanol (12.5 mL). The reaction vessel is evacuated and purged three times with carbon monoxide gas. A balloon filled with carbon monoxide gas is used to maintain the carbon monoxide atmosphere. The reaction mixture is heated at 80° C. for 8 hr. After cooling H2O (50 mL) is added. The mixture is extracted with hexanes (2×50 mL). The combined organic layers are dried over Na2SO4, filtered, concentrated and chromatographed with 0–3% EtOAc in hexanes. 1.24 g (28%) of methyl 2-chloro-4-methylbenzoate is isolated as a colorless oil. EIMS m/e 184 (M+; 35Cl) and 186 (M+; 37Cl).

Provenance & Evidence