3-Bromo-4-chlorobenzamide → 3-Bromo-4-chlorobenzylamine

Temperature

60 °C

To 3-bromo-4-chlorobenzamide (1.6 g, 6.8 mmol) in THF (10 mL) was added borane dimethyl sulfide complex (1.36 mL, 13.6 mmol) at room temperature. The mixture was then heated to 60° C. for 8 days. The solvent was pumped off and the reaction cautiously quenched with ethanol. When bubbling ceased, 1N HCl was added until the pH was ˜2. The mixture was stirred at 50° C. for 4 h. The mixture was partitioned between EtOAc and water. The aqueous phase was washed 3× with EtOAc. The aqueous phase was then adjusted to pH 10 with 2N NaOH and extracted 3× with EtOAc. The combined organics phases were washed with brine, dried over anhydrous Na2SO4, filtered, and evaporated to afford the title compound as a clear oil. LC-MS m/z 219.6 (M+H)+, 1.41 min (ret time).

1. customthe reaction
2. customcautiously quenched with ethanol
3. customWhen bubbling
4. addition1N HCl was added until the pH was ˜2
5. customThe mixture was partitioned between EtOAc and water
6. washThe aqueous phase was washed 3× with EtOAc
7. extractionextracted 3× with EtOAc
8. washThe combined organics phases were washed with brine
9. dry with materialdried over anhydrous Na2SO4
10. filtrationfiltered
11. customevaporated

ORD record

ord-2111612c195645ad9d92bbf8fd1a5fc4

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071588B2