2-[(4-bromophenyl)amino]ethan-1-ol synthesis
- Product Name:2-[(4-bromophenyl)amino]ethan-1-ol
- CAS Number:55110-99-1
- Molecular formula:C8H10BrNO
- Molecular Weight:216.08
Yield:55110-99-1 96%
Reaction Conditions:
with aluminum oxide;copper;potassium hydroxide for 0.5 h;
Steps:
2-(4-Bromophenylamino)ethanol (3j)
General procedure: Iodobenzene (1 mmol), ethanolamine (3 mmol), KOH (3.7 mmol) and Cu0 powder (1 mmol, 63 mg) werestirred for different times (15 min, 25 min, 30 min, 1 hr, 2 hrs, 3 hrs, 4 hrs, 1 day, 2 days). The crudeproduct was dissolved in CH2Cl2 (2 mL) and filtered on Büchner funnel with a sintered glass disc usingCH2Cl2. The solvent was evaporated in vacuum, the crude product was dried and analyzed by GC-MS. Themixture was purified by flash chromatography on silica gel (CH2Cl2-methanol-ammonia) to afford thedesired product. The pure product was analyzed by 1H, 13C NMR spectroscopy and MALDI-TOF massspectrometry after dissolution in an appropriate solvent. 1H NMR (300 MHz, CDCl3): δ 7.18 (2 H, d, J = 9 Hz), 6.43 (2 H,d, J = 9 Hz), 3.73 (2 H, t, J = 6 Hz), 3.17 (2 H, t, J = 3 Hz) ppm; 13C NMR (75 MHz, CDCl3): δ 147.56,132.37, 115.15, 109.79, 61.44, 46.42 ppm. 1H NMR (300 MHz, CDCl3) and 13C NMR (75 MHz, CDCl3)were in accordance with the reported values in literature [3] m/z (MALDI-TOF MS): calcd for C8H10BrNO[M + H]+: 217.9945, found: 217.9946.
References:
Martina, Katia;Rinaldi, Laura;Baricco, Francesca;Boffa, Luisa;Cravotto, Giancarlo [Synlett,2015,vol. 26,# 20,art. no. ST-2015-S0499-C,p. 2789 - 2794]
67-56-1
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