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, Then additional 1.5 M borane in THF (30 mL, 45 mmols) was added and refluxing was 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. Reaction worked up by the cautious addition of ethanol followed by 1N HCl until the pH was 2. The 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 evaporated to give the title compound.

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

ORD record

ord-be3d03020e2341cca3edef3e8611d14b

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071588B2