Sodium Nitrite → 3-Hydroxy-5-(pentafluorosulfanyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

3-Amino-5-pentafluorosulfanylbenzoic acid (1.5 g, example 2a)) was dissolved in 35% sulfuric acid (45 ml) and cooled to −5° C., and a solution of sodium nitrite (387 mg) in water (40 ml) was added dropwise within 10 min. After 40 min, the cooling bath was removed and the mixture was heated to 100° C. After 4 h, the mixture was cooled and the solution was decanted. The clear acidic solution was extracted five times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The crude product was crystallized from ethyl acetate/heptane. 1 g of the desired compound was obtained.

Provenance & Evidence