- 1
[ 65417-74-5 ]

[ 67496-29-1 ]
Yield | Reaction Conditions | Operation in experiment |
80% |
With hydrogenchloride; zinc In tetrahydrofuran; waterReflux |
To a solution of the desired hydroxylamine (7 mmol, 1 eq.) in THF (80 mL) wasadded HCl (2N, 35.3 mL; 70.7 mmol, 10 eq.), followed by zinc (4.62 g, 70.7 mmol, 10 eq.). The mixturewas vigorously stirred under reflux until complete conversion. The mixture was then cooled, filtered on acelite pad and concentrated under reduce pressure to remove THF. The aqueous layer was extracted with EtOAc (30 mL) and the pH of the aqueous layer was adjusted to >10 by addition of a saturated ammoniasolution, then extracted with EtOAc (3x 30 mL). These last organic layers were combined and dried overanhydrous K2CO3, filtered and evaporated to give a crude, which was purified by flash columnchromatography on silica gel (eluent: EtOAc/2percent Et3N).2-Bromo-4,5-dimethoxybenzylamine (7) was obtained (1.43 g, 83percent yield) as a white powder. "H NMR(300 MHz, CDCl3): (ppm) 6.98 (s, 1H), 6.89 (s, 1H), 3.85-3.81 (m, 8H). 13C-NMR (75 MHz, CDCl3) (ppm) 148.5, 148.4, 134.2, 115.6, 113.2, 112.0, 56.2, 56.0, 46.6. |
Reference:
[1] Synlett, 1999, # 4, p. 501 - 503
[2] Tetrahedron Asymmetry, 2006, vol. 17, # 4, p. 642 - 657
[3] Heterocycles, 2014, vol. 88, # 1, p. 807 - 815
[4] Journal of Organometallic Chemistry, 1985, vol. 281, p. 389 - 396
[5] Organic Letters, 2018, vol. 20, # 2, p. 441 - 444
- 2
[ 15930-53-7 ]

[ 67496-29-1 ]
Reference:
[1] Journal of the American Chemical Society, 1997, vol. 119, # 25, p. 5773 - 5784
[2] Tetrahedron Asymmetry, 2006, vol. 17, # 4, p. 642 - 657
[3] Organic Letters, 2006, vol. 8, # 7, p. 1395 - 1398
[4] Chemistry - An Asian Journal, 2014, vol. 9, # 9, p. 2628 - 2634,7
[5] Heterocycles, 2014, vol. 88, # 1, p. 807 - 815
[6] Organic Letters, 2018, vol. 20, # 2, p. 441 - 444