Reaction #1747900

Reaction equation

Bromine

4-(2-hydroxyethyl)-2-methoxypyridine

NaOH

→

5-bromo-4-(2-hydroxyethyl)-2-methoxypyridine

Yield 91.0%

Solvents

ethanol

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (50 mL×3)
2. 2
   Washwashed with 5% aq. NaHSO3 and brine
3. 3
   Dryingdried (Na2SO4)
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue was purified by chromatography with hexane/EtOAc (4:1)

Procedure

Bromine (2.95 g, 18.4 mmol) was slowly added to a stirred solution of 4-(2-hydroxyethyl)-2-methoxypyridine (1.4 g, 9.2 mmol) in 15 mL of absolute ethanol at 0° C., and the reaction mixture was stirred at this temperature for 30 min. The mixture was neutralized by the addition of 2 N aq. NaOH and extracted with EtOAc (50 mL×3). The organic layers were combined and washed with 5% aq. NaHSO3 and brine, dried (Na2SO4), and concentrated. The residue was purified by chromatography with hexane/EtOAc (4:1) to afford 5-bromo-4-(2-hydroxyethyl)-2-methoxypyridine (1.93 g, 91%). 1H NMR (CDCl3) δ 8.14 (s, 1H), 6.68 (s, 1H), 3.86 (s, 3H), 3.85 (t, 2H, J=6.6 Hz), 3.13 (br s, 1H), 2.90 (t, 2H, J=6.6 Hz); 13C NMR (CDCl3) δ 163.27, 149.24, 148.00, 114.41, 112.60, 60.56, 53.63, 38.34.

Source