Ethanol → (3-Bromo-4-methylphenyl)methanamine

Temperature

50 °C

To 3-bromo-4-methylbenzamide (2.14 g, 10 mmol) in THF (10 mL) was added borane dimethyl sulfide complex (2 mL, 20 mmol) at 0° C. The mixture was then heated to 50° C. for 16 h. Additional borane dimethyl sulfide complex (1 mL, 10 mmol) was added and heating continued at 60° C. for an additional 5 days. The reaction mixture was cooled to room temperature and ethanol was cautiously added. When bubbling ceased, 1N HCl was added until the pH was ˜2. This mixture was stirred at 50° C. for 4 h. The mixture was partitioned between EtOAc and water. The aqueous was washed 3× with EtOAc. 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 evaporated to afford the title compound. LC-MS m/z 199.8 (M+H)+, 1.01 min (ret time).

1. additionAdditional borane dimethyl sulfide complex (1 mL, 10 mmol) was added
2. temperatureheating
3. temperatureThe reaction mixture was cooled to room temperature
4. customWhen bubbling
5. addition1N HCl was added until the pH was ˜2
6. customThe mixture was partitioned between EtOAc and water
7. washThe aqueous was washed 3× with EtOAc
8. extractionextracted 3× with EtOAc
9. dry with materialThe combined organics phases were dried over anhydrous Na2SO4
10. filtrationfiltered
11. customevaporated

ORD record

ord-29a9e62ebd38405ab856eb3de86c6faf

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071588B2