Borane → 2-(Aminomethyl)-5-bromoaniline
Reaktionsgleichung
[NH2:1][C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].B>C1COCC1>[NH2:5][CH2:4][C:3]1[CH:6]=[CH:7][C:8]([Br:10])=[CH:9][C:2]=1[NH2:1]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of compound (11) (2 g, 10.0 mmol) in dry THF at 0° C. under an argon atmosphere was slowly added borane (15 mL, 1.0 M in THF). The reaction mixture was stirred for 10 min at 0° C. and further 72 h at room temperature. The reaction mixture was cooled to 0° C. and quenched by addition of ethanol (96%). The resulting suspension was extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over sodium sulfate. Ethyl acetate was completely removed under reduced pressure and the residues were chromatographed over silica column, eluting with ethyl acetate:hexanes (1:1) and changing to (100%) afforded 1.73 g (85%) of compound (12) as a dark brown thick gum. IR (KBr) νmax. cm−1: 3438, 3318 (NH2), 3052 (Ar—H), 2911 (Alph-H), 1604, 1512, 1416 (C═C). 1H NMR (500 MHz, CDCl3) δ=4.19 (s, 2H, NH2); 4.42 (s, 2H, CH2); 6.52 (d, 1H, J=8.2 Hz, H-3); 7.16 (dd, 1H, J=2.2, 8.2 Hz, H-4); 7.18 (d, 1H, J=2.2 Hz, H-6); 13C NMR (125.7 MHz, CDCl3) δ=63.78 (CH2), 109.56 (C-2), 117.51 (C-6), 126.57 (C-5), 131.58 (C-3/C-4), 131.86 (C-3/C-4), 145.06 (C-1). Calculated (%) for C7H9BrN2 (199.99); C: 41.82, H: 4.51, N: 13.93. found (%); C: 41.74, H: 4.58, N: 13.84.