Boron tribromide → 2-Methylbenzofuran-6-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-Methoxy-2-methyl-benzofuran 125-A (1.76 g, 10.85 mmol) in 45 ml of CH2Cl2 at −5° C. was added BBr3 (24 ml of 1M BBr3 in CH2Cl2, 16.28 mmol). The reaction was allowed to warm to 0° C. and stirred at that temperature for 1.5 hr. The reaction was poured into a mixture of ice and saturated aqueous NaHCO3 and layers were separated. The aqueous layer was re-extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to a brown oil. The residue was chromatographed on silica gel eluting CH2Cl2 to give 872 mg (54%) of 6-Hydroxy-2-methyl-benzofuran 125-B. Anal calc'd for C9H8O2: C, 72.96; H, 5.44. Found: C, 72.72; H, 5.43.

Provenance & Evidence