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0 °C

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).

1. additionwas added as a solid in small portions
2. customThe mixture was then quenched with water (200 mL)
3. additiondiluted with EtOAc (300 mL)
4. customtransferred to a separatory funnel
5. washThe organic layer was washed with dilute aqueous NaOH, water and brine
6. dry with materialdried over Na2SO4
7. filtrationFiltration of the solids and removal of the solvent