Methyl iodide → (6-Bromo-5-methoxypyridin-2-yl)methanol

HRID 922373Notes

Reaction equation

HRID 922373 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH2:9][OH:10])[N:3]=1.[C:11]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[Br:1][C:2]1[N:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 160446662-Bromo-6-(hydroxymethyl)pyridin-3-ol

Product 1

HCID 16044667(6-Bromo-5-methoxypyridin-2-yl)methanolYield 156.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-bromo-6-(hydroxymethyl)pyridin-3-ol (2.04 g, 10 mmol) and K2CO3 (2.07 g, 15 mmol) in acetone (50 mL) was added iodomethane (1.84 g, 13 mmol) at rt. The reaction mixture was refluxed for 4 h. After that time the reaction was cooled to rt, filtered to remove solids and concentrated under reduced pressure to give (6-bromo-5-methoxypyridin-2-yl)methanol (3.42 g, >99%) as a white solid: 1H NMR (400 MHz, CDCl3): δ 7.25 (d, J=8.0 Hz, 1H), 7.16 (d, J=8.4 Hz, 1H), 4.70 (s, 2H), 3.93 (s, 3H), 2.78 (br s, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. filtrationfiltered
  3. customto remove solids
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c87d88417a845b2a52c04d31f6bbd0b
Source dataset
uspto-grants-2016_03
Patent number
US09278940B2

Reaction notes

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