Dichloromethane → Ethyl 5-bromo-6-methoxy-3-pyridineacetate

HRID 554654Notes

Reaction equation

HRID 554654 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]#N)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].[C:13](Cl)(=[O:15])[CH3:14].C(Cl)Cl.C([O-])(O)=[O:21].[Na+]>CCO>[CH2:13]([O:15][C:11](=[O:21])[CH2:10][C:4]1[CH:5]=[N:6][C:7]([O:8][CH3:9])=[C:2]([Br:1])[CH:3]=1)[CH3:14]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 585393925-Bromo-6-methoxy-3-pyridineacetonitrile

Product 1

HCID 58539686Ethyl 5-bromo-6-methoxy-3-pyridineacetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To (5-bromo-6-methoxy-pyridin-3-yl)-acetonitrile (1.139 g, 5.02 mmol) in EtOH (11 ml) was added acetyl chloride (3.6 mL, 50.54 mmol), and the reaction was stirred at 50° C. for 24 hours, and at room temperature for 2 days. The reaction was worked up with CH2Cl2 and saturated aqueous NaHCO3, and then reacidified and extracted with CH2Cl2. The combined organic layers were dried, filtered, and concentrated to give (5-bromo-6-methoxy-pyridin-3-yl)-acetic acid ethyl ester.

Workup

  1. waitat room temperature for 2 days
  2. extractionextracted with CH2Cl2
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eb442a421b1f46e3bd94fe6b1a2559e9
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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