Borane → 3-Bromo-5-methoxybenzenemethanamine

Temperature

70 °C

3-Bromo-5-methoxybenzonitrile (13.1 g, 61.8 mmol) was dissolved in dry tetrahydrofuran (100 mL) in a flame-dried flask and cooled in an ice bath. A solution of borane in tetrahydrofuran (100 mL, 0.10 mol, 1.0 M) was slowly added over a period of 30 minutes. After the addition was complete, the mixture was heated at 70° C. overnight and quenched slowly with ice water and Na2CO3 (saturated aqueous solution). After removal of THF, the residue was extracted with large amounts of EtOAc three times. The combined organic layers were washed with water, dried, and concentrated to give the crude product, which was purified by silica gel column chromatography to give the desired product as a white powder (2.57 g, 19%). LCMS for C8H10BrNO (M+H)+: m/z=216.9, 218.9.

1. temperaturecooled in an ice bath
2. additionAfter the addition
3. customquenched slowly with ice water and Na2CO3 (saturated aqueous solution)
4. customAfter removal of THF
5. extractionthe residue was extracted with large amounts of EtOAc three times
6. washThe combined organic layers were washed with water
7. customdried
8. concentrationconcentrated
9. customto give the crude product, which
10. customwas purified by silica gel column chromatography

ORD record

ord-e3acce5bc11b4d48837af5410db73ba2

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765727B2