Boron tribromide → HCID 59853453, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of alcohol 38 (56 mg, 0.15 mmol) in CH2Cl2 (2 mL) was added 1M BBr3 in CH2Cl2 at 0° C. See Scheme 22 (FIG. 24). After the reaction mixture was stirred for 1 h at 0° C., the mixture was partitioned between CH2Cl2 and sat. NaHCO3. The aqueous phase was neutralized with solid NaHCO3 and extracted with CH2Cl2 and EtOAc. The organic phase was dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude product was chromatographed on silica gel (eluting 5-10% MeOH/CH2Cl2) to give 3-(2-hydroxymethyl-5-isopropyl-3-pyridin-4-ylmethyl-3H-imidazol-4-ylsulfanyl)-phenol 39 (43 mg, 81%) as a colorless solid.

Provenance & Evidence