Hydrochloric Acid → 1-(2-BROMOPHENYL)CYCLOPROPANAMINE

Temperature

-78 °C

Ethyl magnesium bromide (20.14 ml, 60.4 mmol) was added dropwise to a stirred, cooled −78° C. mixture of 2-bromobenzonitrile (5.0 g, 27.5 mmol) and titanium isopropoxide (8.59 g, 30.2 mmol) in ether (100 ml) and the mixture was stirred at −78° C. for 10 minutes. The yellow solution was warmed to ambient temperature and held for 1 hour. Boron trifluoride etherate (7.8 g, 54.9 mmol) was added dropwise and the mixture was stirred for 1 hour. 1 N HCl (90 ml) was added and the mixture was stirred for 10 minutes. Added 300 ml 1N NaOH and then extracted with ether. The organic portion was washed with brine, dried (MgSO4) and the solvent removed in vacuo. Purification by flash chromatography on 80 g of silica, eluting with a gradient of 0-100% EtOAc in hexanes afforded 0.80 g, 14% of 7-1 as yellow oil.

1. temperatureThe yellow solution was warmed to ambient temperature
2. waitheld for 1 hour
3. stirringthe mixture was stirred for 1 hour
4. stirringthe mixture was stirred for 10 minutes
5. extractionextracted with ether
6. washThe organic portion was washed with brine
7. dry with materialdried (MgSO4)
8. customthe solvent removed in vacuo
9. customPurification by flash chromatography on 80 g of silica
10. washeluting with a gradient of 0-100% EtOAc in hexanes

ORD record

ord-a8e85dea891a4302875dadab4272c9fe

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119681B2