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 the 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 layer 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 dried over anhydrous Na2SO4, filtered, and evaporated 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. addition1N HCl was added until the pH was ˜2
4. customThe mixture was partitioned between EtOAc and water
5. washThe aqueous layer was washed 3× with EtOAC
6. extractionextracted 3× with EtOAc
7. dry with materialThe combined organics phases were dried over anhydrous Na2SO4
8. filtrationfiltered
9. customevaporated

ORD record

ord-72c1d7f760884c57964d82a4913909b8

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071588B2