3-Bromo-5-chlorobenzamide → (3-Bromo-5-chlorophenyl)methanamine

Temperature

60 °C

To 3-bromo-5-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 7 days. The solvent was pumped off and the reaction cautiously quenched with ethanol. When bubbling ceased, 1N HCl was added until pH was ˜2. The mixture was stirred at 50° C. for 4 h. The mixture was partitioned between EtOAc and water. The aqueous was washed 3× with ethyl acetate. The aqueous was then adjusted to pH 10 with 2N NaOH and extracted 3× with EtOAc. The combined organics phases were dried over anhydrous Na2SO4, filtered, and concentrated to give the title compound as a clear oil. LC-MS m/z 219.7 (M+H)+, 1.42 min (ret time).

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

ORD record

ord-b21dc01c142543e3b5d531ceadb26227

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067408B2