Hydrogen Bromide → HCID 19983091, compound

Participants

Reaction Steps

A mixture of α,α-bis(4-fluorophenyl)-1-[(4-methylphenyl)sulfonyl]-3-pyrrolidineacetonitrile (16.6 g, 0.0367 mole), phenol (50 g, 0.53 mole) and 300 ml of 48% hydrobromic acid was heated at reflux for two hours. The reaction mixture was cooled to room temperature and made alkaline with ice/50% sodium hydroxide. The aqueous layer was extracted with chloroform. The chloroform layer was back extracted with 5% sodium hydroxide, dried over sodium sulfate and filtered, and solvent was removed to produce a dark brown oil. The dark-brown oil was dissolved in chloroform and extracted with 1N sulfuric acid. This acidic layer was discarded. The chloroform layer was extracted with base, and the solvent was removed to give a dark brown oil. This oil was converted to the oxalate, and the salt was recrystallized from methanol-diethyl ether. A white solid was isolated and dried in vacuo overnight at 80° C. This produced 7.17 g (49%) of off-white solid, mp 88.5°-90° C.

Provenance & Evidence