Phenol → HCID 59816114, compound

Participants

Reaction Steps

To a 0 C solution of the phenol (26.7 g, 114 mmol) and benzyl bromide (20.5 mL, 171 mmol) in DMF (300 mL) add NaH (6.84 g, 1.5 mmol) portionwise over 15 min. Allow venting during the addition, during which time the solution turns dark red. After 30 min, remove the cooling bath and allow the solution to warm to 23 C, during which time a precipitate forms and the solution turns dark brown. After 2 h, slowly pour the solution into ½ satd. NaHCO3 (500 mL), and filter the mixture. Wash the filter cake with H2O (2×300 mL) and 50% Et2O/hexanes (2×300 mL.) to remove remaining aqueous salts and excess benzyl bromide. Dry the remaining yellow solid to afford Preparation 27 (28.9 g, 78%). 1H NMR (d-DMSO) δ 8.67 (s, 1 H), 7.57 (s, 1 H), 7.37-7.47 (m, 7 H), 5.15 (s, 2 H), 4.28 (q, J=7.2 Hz, 2 H), 1.31 (t, J=7.2 Hz, 3 H).

Provenance & Evidence