Iodoethane → 3-Bromo-5-(ethoxymethyl)pyridine

HRID 1175594Notes

Reaction equation

HRID 1175594 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]([CH2:10][OH:11])[CH:7]=[N:8][CH:9]=1.[CH2:12](I)[CH3:13]>CS(C)=O.O>[Br:3][C:4]1[CH:9]=[N:8][CH:7]=[C:6]([CH2:10][O:11][CH2:12][CH3:13])[CH:5]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 219843463-Bromo-5-(ethoxymethyl)pyridineYield 97.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a mixture of powdered KOH (5.96 g, 106.4 mmol) in anhydrous DMSO (20 mL) was added under argon a solution of (5-bromopyridin-3-yl)methanol (example 26c) (5 g, 26.6 mmol) in anhydrous DMSO (20 mL), followed by EtI (2.6 mL, 31.9 mmol). The reaction mixture was stirred at room temperature for 1 hour then diluted with water and extracted with EtOAc. The organic phase was washed with water and brine, dried over MgSO4, filtered and evaporated to give 5.6 g of 3-bromo-5-(ethoxymethyl)pyridine as a dark brown oil in 97% yield. 1H NMR (400 MHz, CDCl3): 1.27 (t, 3H), 3.57-3.59 (q, 2H), 4.50 (s, 2H,), 8.48 (s, 1H), 8.60 (s, 1H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b0fc68d212864d28ab67f0adc971d569
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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