1,2-Dimethoxyethane → 1-Phenylisoquinoline

Participants

Reaction Steps

1-Chloroisoquinoline (5.0 g, 30 mmol) and phenylboronic acid (4.5 g, 37 mmol) was dissolved into 100 mL of ethylene glycol dimethyl ether, followed by the addition of triphenylphosphine (0.7 g, 3 mmol) and Pd(II) acetate (0.17 g, 0.75 mmol). The reaction mixture was refluxed for 16 hours. The reaction mixture was cooled and the aqueous layer discarded. Additional ethyl acetate was added and the solvent was washed with a saturated solution of sodium chloride, dried over magnesium sulfate and concentrated to give 1-phenylisoquinoline (5.0 g, 79% yield)

Provenance & Evidence