Sodium Hydroxide → HCID 10889767, compound

HRID 1660718Notes

Reaction equation

HRID 1660718 reaction equation
[Br:1]Br.[OH:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH3:13])[CH:7]=1.[OH-].[Na+]>C(O)C>[Br:1][C:11]1[C:6]([CH2:5][CH2:4][OH:3])=[CH:7][C:8]([O:12][CH3:13])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 15319874HCID 15319874, compound

Product 1

HCID 10889767HCID 10889767, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. extractionextracted with EtOAc (50 mL×3)
  2. washwashed with 5% aq. NaHSO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography with hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-d604353ae2b24a1e83089254514273a7
Source dataset
uspto-grants-2011_10
Patent number
US08030300B2

Reaction notes

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