Hydrochloric Acid → HCID 57937816, compound

Participants

Reaction Steps

4-Bromo-3-fluoro-N-(3-methylbutyl)benzamide (I-5a: 2.6 g, 9.02 mmol) was dissolved in tetrahydrofuran (20 ml) and treated with 1M borane in tetrahydrofuran (20 ml, 18.04 mmol) at room temperature. After heating at reflux for 24 hours, the reaction mixture was carefully treated with concentrated HCl and then heated at reflux for 1 additional hour. After cooling to ambient temperature, the reaction mixture was filtered and the resulting solid suspended in 1N aqueous NaOH and the mixture extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The resulting material used in the subsequent reaction without further purification.

Provenance & Evidence