3-Bromo-2-chloro-5-methylpyridine → 3-Bromo-2-ethoxy-5-methylpyridine

HRID 2271461Notes

Reaction equation

HRID 2271461 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[O-:10][CH2:11][CH3:12].[Na+]>C(O)C.O>[Br:1][C:2]1[C:3]([O:10][CH2:11][CH3:12])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 2

HCID 2854373-Bromo-2-chloro-5-methylpyridineHCID 2723922Sodium ethoxide

Product 1

HCID 225911753-Bromo-2-ethoxy-5-methylpyridineYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-bromo-2-chloro-5-methylpyridine (4.00 g, 19.37 mmol) in ethanol (100 mL) was added sodium ethoxide (6.59 g, 96.9 mmol) in three portions. The mixture was stirred under nitrogen at 100° C. for 2 days. The reaction was cooled to room temperature, diluted with water and extracted with DCM. The combined organic layers were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification (FCC, SiO2, 20%, EtOAc/hexanes) afforded the title compound (3.00 g, 72%). 1H NMR (400 MHz, DMSO-d6) δ 7.94 (dd, J=0.8, 2.3 Hz, 1H), 7.89-7.82 (m, 1H), 4.31 (q, J=7.0 Hz, 2H), 2.18 (t, J=0.8 Hz, 3H), 1.30 (t, J=7.0 Hz, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. customthe solvent was removed under reduced pressure
  5. customPurification (FCC, SiO2, 20%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-3adbdd4e54e94d8da9784b6278f11577
Source dataset
uspto-grants-2015_09
Patent number
US09120770B2

Reaction notes

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