反应详情

To a stirred solution of 2-(3-methoxyphenyl)ethylamine (10.0 g, 66.2 mmol) in dry CH2Cl2 (100 mL) at −78° C. was added a 1M solution of BBr3 in CH2Cl2 (200 mL, 3 eq.) and the solution was allowed to slowly warm to RT. After stirring for 3 h at RT the resulting precipitate was filtered off, washed with CH2Cl2 (200 mL) and dried. The off-white solid was dissolved in cold H2O (50 mL) and the insoluble material was filtered off. The acidic filtrate (pH 1.2) was made basic (pH 13.0) with 10 N NaOH and the resulting yellow solution was extracted with ether (100 mL) and the organic layer was discarded. The aqueous layer was re-acidified with conc. HCl to pH 1.5 and then made alkaline (pH 9–10) with conc. NH4OH. The aqueous layer was then extracted with n-butanol (2×150 mL), dried (K2CO3) and concentrated to dryness to afford a viscous oil. The oily residue was then dissolved in MeOH (10 mL) and a solution of saturated HCl/MeOH was added. The solution was concentrated to small volume and ether was added to give a precipitate. The ether was decanted off to afford the desired compound as an off white solid (6.5 g, 57%). 1H NMR (D2O) 2.79 (t, 2H, J=7.2 Hz), 3.08 (t, 2H, J=7.2 Hz), 6.60–6.78 (m, 3H), 7.11 (t, 1H, J=7.7 Hz).

1. filtrationwas filtered off
2. washwashed with CH2Cl2 (200 mL)
3. customdried
4. dissolutionThe off-white solid was dissolved in cold H2O (50 mL)
5. filtrationthe insoluble material was filtered off
6. extractionthe resulting yellow solution was extracted with ether (100 mL)
7. extractionThe aqueous layer was then extracted with n-butanol (2×150 mL)
8. dry with materialdried (K2CO3)
9. concentrationconcentrated to dryness
10. customto afford a viscous oil
11. concentrationThe solution was concentrated to small volume and ether
12. additionwas added
13. customto give a precipitate
14. customThe ether was decanted off