Toluene → HCID 57423400, compound

Participants

Reaction Steps

To a mixed solution of 42 mL of toluene, 16 mL of ethanol and 7.8 mL of water containing 5.2 g of methyl 4-bromo-2-nitrobenzoate, 2.9 g of dihydroxyphenyl borane, 4.2 g of sodium hydrogen carbonate and 1.1 g of tetrakis(triphenylphosphine)-palladium (0) were added sequentially and the resulting mixture was heated to reflux under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, 1.1 g of tetrakis(triphenylphosphine)palladium (0) was added to the reaction mixture and the resulting mixture was heated to reflux under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, 1.1 g of tetrakis(triphenylphosphine)palladium (0) was added to the reaction mixture and the resulting mixture was heated to reflux under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, water was added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 1.0 mol/L hydrochloric acid and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=20:1] to obtain 4.8 g of methyl 2-nitro-4-phenylbenzoate as pale yellow oil.

Provenance & Evidence