4-(Bromomethyl)phenylacetic acid → 2-[4-(Aminomethyl)phenyl]ethan-1-ol

Temperature

70 °C

To a stirred solution of NH3/EtOH (170 mL) was added (4-Bromomethyl-phenyl)-acetic acid (1.61 g, 7.01 mmol). The resultant solution was stirred at room temperature for 2 h. The mixture was concentrated in vacuo, and redissolved with anhydrous THF (10 mL). To the solution, BH3.Me2S was added, and the mixture was stirred for 1 h at 70° C., and at room temperature for 2 d. The reaction was concentrated in vacuo, 6 N HCl (10 mL) was added, and the mixture was stirred at 70° C. for 1 h. Water (20 mL) was added, and it was neutralized with 1 N NaOH to pH˜7. The solution was concentrated to dryness under high vacuum, washed with MeOH/CH2Cl2, and filtered. The crude product was purified by flash chromatography on silica gel (5:3:92 CH3OH—NH3 H2O—CH2Cl2) to afford the title compound (820 mg, 77%) as a white foam.

1. concentrationThe mixture was concentrated in vacuo
2. dissolutionredissolved with anhydrous THF (10 mL)
3. additionMe2S was added
4. waitat room temperature for 2 d
5. concentrationThe reaction was concentrated in vacuo, 6 N HCl (10 mL)
6. additionwas added
7. stirringthe mixture was stirred at 70° C. for 1 h
8. additionWater (20 mL) was added
9. concentrationThe solution was concentrated to dryness under high vacuum
10. washwashed with MeOH/CH2Cl2
11. filtrationfiltered
12. customThe crude product was purified by flash chromatography on silica gel (5:3:92 CH3OH—NH3 H2O—CH2Cl2)

ORD record

ord-f39523ae1dee437e8037402bd661af82

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07312234B2