Sulfuric Acid → 5-Bromo-2-cyclopropylphenol

Participants

Reaction Conditions

Reaction Steps

An ice-cold solution of H2SO4 (0.23 mL, 4.31 mmol) in water (2 mL) was added to 5-bromo-2-cyclopropylaniline (300 mg, 1.42 mmol) at 0° C. The reaction was stirred for 10 min, then sodium nitrite (98 mg, 1.415 mmol) in 2 mL cold water was added dropwise. The reaction was stirred at 0° C. for 1 h and then heated at 100° C. for 1 h. Reaction was extracted with EtOAc. Combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to afford the title compound, which was used without further purification. LC-MS calculated for C9H9BrO: 211.98, no ionization, (Rt: 1.57/4 min.).

Provenance & Evidence