PYRIDINE,3,5-BIS(BROMOMETHYL)- synthesis
- Product Name:PYRIDINE,3,5-BIS(BROMOMETHYL)-
- CAS Number:35991-75-4
- Molecular formula:C7H7Br2N
- Molecular Weight:264.95
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Yield: 95%
Reaction Conditions:
Stage #1:3,5-bis(hydroxymethyl)pyridine with hydrogen bromide in water at 125;
Stage #2: with sodium hydrogencarbonate in water; pH=8
Steps:
12
Example 12 3,5-Bis(bromomethyl)pyridine. To pyridine-3,5-diyldimethanol (2 g, 14 mmol) was added 60% HBr (15 mL) slowly. The reaction was heated at 125° C. for 6 h then cooled to room temperature. The resulting residue was dissolved in H2O (50 mL) to give a yellow solution. To this solution was added saturated NaHCO3 to pH 8. The resulting aqueous solution was extracted with CH2Cl2 (4×50 mL), and the combined organic layers were dried over Na2SO4. The solvent was removed by rotary evaporation, and the resulting material was purified by flash column chromatography (EtOAc/hexanes, 1:4) to yield 3,5-bis(bromomethyl)pyridine (3.5 g, 95%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 4.45 (s, 4H), 7.74-7.75 (t, J=2.0 Hz, 1H), 8.53-8.54 (d, J=2.0 Hz, 2H); 13C NMR (125 MHz, CDCl3) δ 29.3, 134.0, 137.3, 149.8; LC-TOF (M+H+) calcd for C7H8Br2N 263.90235, found 263.90182.
References:
Silverman, Richard B.;Xue, Fengtian US2010/203613, 2010, A1 Location in patent:Page/Page column 9
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