Sodium Hydroxide → (3-Bromo-6-methoxy-2-methylpyridin-4-yl)methanol

HRID 1043911Notes

Reaction equation

HRID 1043911 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[C:5]([CH3:11])[N:4]=1.C1C(=O)N([Br:19])C(=O)C1.[OH-].[Na+]>C(O)(=O)C>[Br:19][C:6]1[C:5]([CH3:11])=[N:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=1[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 53804368(2-Methoxy-6-methylpyridin-4-yl)methanol

Product 1

HCID 86686342(3-Bromo-6-methoxy-2-methylpyridin-4-yl)methanolYield 79.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (2-methoxy-6-methylpyridin-4-yl)methanol (1.1 g) and NBS (1.34 g) was stirred in an acetic acid solvent (22 mL) at room temperature for 12 hours. A 5 M aqueous sodium hydroxide solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 50%) to give the title compound (1.32 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 50%)

Sources & evidence

ORD record
ord-544de50833394a949f307257ff480d61
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

Loading…