Hydrochloric Acid → (3-Bromo-4-methoxyphenyl)methanamine

Temperature

50 °C

3-Bromo-4-(methyloxy)benzonitrile (2.12 g, 10 mmol), THF (30 mL), and 1.5 M borane in THF (30 mL, 45 mmols) were combined and stirred under argon at reflux. The additional 1.5 M borane in THF (30 mL, 45 mmols) and reflux continued. THF (30 mL), and 1.5 M borane in THF (30 mL, 45 mmols) was again added and the mixture refluxed for a total of ten days to drive the reaction to completion. The reaction was worked up by the cautious addition of ethanol followed by 1N HCl until the pH was 2. This mixture was then heated to 50° C. for 4 h. The solvents were pumped off, and the residue partitioned between EtOAc and water. The aqueous phase was washed 3× with EtOAc and adjusted to pH 10 by the addition of 2.5 N NaOH. The aqueous phase was extracted 3× with EtOAc. The combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated to give the title compound. LC-MS m/z 198.7 (M−NH2), 0.99 min (ret time).

1. temperatureat reflux
2. temperaturethe mixture refluxed for a total of ten days
3. customthe reaction to completion
4. customthe residue partitioned between EtOAc and water
5. washThe aqueous phase was washed 3× with EtOAc
6. additionadjusted to pH 10 by the addition of 2.5 N NaOH
7. extractionThe aqueous phase was extracted 3× with EtOAc
8. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-49cc177301fa4a26926a7c90e5ac8efe

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067408B2