Phenol → Dibenzyl ether

Participants

Reaction Conditions

Reaction Steps

A solution of benzyl bromide (128 mg, 0.75 mmol), phenol compound 40 (131.5 mg, 0.50 mmol), and potassium carbonate (138 mg, 1.00 mmol) in DMF (3.0 mL) was heated to 60° C. for 1.5 h. After cooling to 23° C., the solution was filtered, concentrated in vacuo, and purified by silica gel chromatography (1:1 EtOAc/hexanes) to give benzyl ether compound 49 (132.5 mg, 75%) as a white solid. mp=124-125° C.; 1H NMR (CDCl3) δ 7.67 (s, 1H), 7.49 (s, 1H), 7.40 (m, 6H), 6.0-5.8 (2 br s, 2H), 5.08 (s, 2H); IR (KBr pellet) 3369, 3192, 1660, 1564 cm−1; Anal. (C14H12INO2) C, H, N.

Provenance & Evidence