Ethyl Acetate → 3-Bromo-5-bromomethyl-2-methoxy-pyridine

HRID 554652Notes

Reaction equation

HRID 554652 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10]O)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].P(Br)(Br)[Br:13].CCOC(C)=O.C([O-])(O)=O.[Na+]>COCCOC>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[N:6][CH:5]=[C:4]([CH2:10][Br:13])[CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 58539347HCID 58539347, compound

Product 1

HCID 585395103-Bromo-5-bromomethyl-2-methoxy-pyridine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To (5-bromo-6-methoxy-pyridin-3-yl)-methanol (2.86 g, 13.1 mmol) in DME (30 mL) was added phosphorus tribromide (1.9 mL, 19.7 mmol), and the reaction was stirred for 15 minutes. The mixture was worked up with EtOAc and saturated aqueous NaHCO3, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give 3-bromo-5-bromomethyl-2-methoxy-pyridine.

Workup

  1. dry with materialthe combined organic layers were dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9c368060408646bdb5a73561c3db981c
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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