HCID 68890072, compound → 2-(4-bromo-2-fluorophenyl)ethanamine

Temperature

0 °C

4-Bromo-2-fluoronitro styrene (1 equivalent) in THF (0.2 M) was cooled to 0° C. and treated with 1.0 M BH3 in THF (5 equivalents). The reaction was heated to reflux overnight. The reaction was cooled to 0° C. and quenched with H2O then 1 N HCl until a pH of about 2 was achieved. The reaction was stirred for 30 minutes at room temperature and then extracted with ether (3×). The aqueous layer was made basic with 5% NaOH solution. The aqueous layer was then extracted into ether (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated to give crude 2-(4-bromo-2-fluorophenyl)ethylamine. Purification by flash chromatography eluting with 2%-5%-10% MeOH/CH2Cl2 gradients containing 1% concentrated ammonia afforded the desired compound. MS m/z 219.8 (M+H).

1. additiontreated with 1.0 M
2. temperatureThe reaction was heated
3. temperatureto reflux overnight
4. customquenched with H2O
5. extractionextracted with ether (3×)
6. extractionThe aqueous layer was then extracted into ether (3×)
7. washThe combined organic layers were washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto give crude 2-(4-bromo-2-fluorophenyl)ethylamine
12. customPurification by flash chromatography
13. washeluting with 2%-5%-10% MeOH/CH2Cl2 gradients
14. additioncontaining 1% concentrated ammonia

ORD record

ord-7ad226db7cc8408f90ce1e903f42d325

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06995269B2