Ethylene Glycol → HCID 58241926, compound

HRID 1524086Notes

Reaction equation

HRID 1524086 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5](Cl)=[N:6][CH:7]=[CH:8][CH:9]=1.[CH2:11]([OH:14])[CH2:12][OH:13]>>[Br:3][C:4]1[C:5]([O:13][CH2:12][CH2:11][OH:14])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 6933243-Bromo-2-chloropyridine

Product 1

HCID 58241926HCID 58241926, compound

Procedure

Sodium hydride (1.6 g, 42 mmol) was added to cooled (ice-water bath) ethane-1,2-diol (5 mL) and the resulting mixture stirred at rt for 30 min before adding 3-bromo-2-chloropyridine (2.0 g, 100 mmol). The mixture was then heated at 130° Celsius under a N2 atmosphere overnight before cooling to rt and subjecting the reaction mixture to FCC purification to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 8.05 (dd, J=4.9, 1.7, 1H), 7.82 (dd, J=7.6, 1.7, 1H), 6.80 (dd, J=7.6, 4.9, 1H), 4.54-4.50 (m, 2H), 3.97 (dd, J=8.8, 5.5, 2H), 3.18 (t, J=5.8, 1H).

Workup

  1. temperatureThe mixture was then heated at 130° Celsius under a N2 atmosphere overnight
  2. temperaturebefore cooling to rt
  3. customto FCC purification

Sources & evidence

ORD record
ord-bcde4ff583e84124a7bc2000f518abc8
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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