Phenol → 6-Iodo4-phenoxyquinazoline

Participants

Reaction Conditions

Reaction Steps

A suspension of NaH (washed free of mineral oil) in DMF (40 mL) was cooled to 0° C. and a solution of phenol (5.65 g, 60 mmol) in DMF (20 mL) was added dropwise. Upon completion of addition, 6-iodo-4-chloroquinazoline 13 (14.6 g, 50.3 mmol) was added as a solid in small portions. The cooling bath was moved and the reaction mixture was stirred at room temperature for 2 hours. The mixture was then quenched with water (200 mL), diluted with EtOAc (300 mL) and transferred to a separatory funnel. The organic layer was washed with dilute aqueous NaOH, water and brine and dried over Na2SO4. Filtration of the solids and removal of the solvent provided 6-iodo4-phenoxyquinazoline 14 (17.2 g, 98%) as a yellow solid. 1H NMR (400 MHz; CDCl3): δ: 8.74 (d, 1H), 8.14 (s, 1H), 8.12 (dd, 1H), 7.71 (d, 1H). 7.49 (dd, 2H), 7.32 (t, 1H), 7.22 (m, 2H).

Provenance & Evidence