ChemicalBook CAS DataBase List 2,6-BIS(BROMOMETHYL)PYRIDINE

2,6-BIS(BROMOMETHYL)PYRIDINE synthesis

9synthesis methods

Product Name:2,6-BIS(BROMOMETHYL)PYRIDINE
CAS Number:7703-74-4
Molecular formula:C7H7Br2N
Molecular Weight:264.95

1195-59-1 Synthesis

1195-59-1
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$6.00/1g

7703-74-4
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$52.00/1g

Yield:7703-74-4 96%

Reaction Conditions:

Stage #1: 2.6-bis(hydroxymethyl)pyridinewith hydrogen bromide in water at 125;
Stage #2: with sodium hydrogencarbonate in water; pH=8;

Steps:

15

Example 15 2,6-Bis(bromomethyl)pyridine. To pyridine-2,6-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 NaHCO₃to 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, 1:9-1:4) to yield 2,6-bis(bromomethyl)pyridine (3.5 g, 96%) as a white solid: ¹H NMR (500 MHz, CDCl₃) δ 4.53 (s, 4H), 7.36-7.38 (d, J=8.0 Hz, 2H), 7.68-7.71 (dd, J=7.5, 8.0 Hz, 1H); ¹³C NMR (125 MHz, CDCl₃) δ 33.8, 123.1, 138.4, 157.0; LC-TOF (M+H⁺) calcd for C₇H₈Br₂N 263.90235, found 263.90193.