Hydrochloric Acid → HCID 57937816, compound

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.

1. temperatureAfter heating
2. temperatureat reflux for 24 hours
3. temperatureheated
4. temperatureat reflux for 1 additional hour
5. filtrationthe reaction mixture was filtered
6. extractionthe mixture extracted twice with ethyl acetate
7. washThe combined organic layers were washed with brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. customevaporated under reduced pressure
11. customThe resulting material used in the subsequent reaction without further purification

ORD record

ord-1fcd553b945240399978630a7938afb1

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07615651B2